Updated on 2024/02/01

写真a

 
IWAMOTO Takahiro
 
Organization
Faculty of Science and Engineering Research Associate
Contact information
The inquiry by e-mail is 《here
External link

Degree

  • 博士(工学) ( 京都大学 )

  • 修士(工学) ( 京都大学 )

Education

  • 2014.3
     

    Kyoto University   doctor course   completed

  • 2011.3
     

    Kyoto University   master course   completed

  • 2009.3
     

    Kyoto University   Faculty of Engineering   graduated

Research History

  • 2020.4 - Now

    Chuo University   Assistant Professor

  • 2014.4 - 2020.3

    Kyoto University   Institute for Chemical Research   Assistant Professor

  • 2011.3 - 2014.4

    日本学術振興会   特別研究員DC1

  • 2011.3 - 2014.4

    日本学術振興会   特別研究員DC1

Professional Memberships

  • 日本化学会

  • 有機合成化学協会

Research Interests

  • 有機合成化学

  • catalyst

  • Organic chemistry

  • 触媒

Research Areas

  • Life Science / Bioorganic chemistry

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry

Papers

  • One‐pot Syntheses of Benzo‐ and Benzofuran‐fused Iridaoxabenzenes via CH Bond Activations of Alkyl‐bridged Diphenol Derivatives

    Takahiro Iwamoto, Mika Suzuki, Hibiki Hasegawa, Hinako Abeta, Yusuke Matsuo, Takayuki Tanaka, Nobuhiro Yasuda, Youichi Ishii

    Chemistry – An Asian Journal   2023.8

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    Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    One‐pot syntheses of new π‐extended metallaaromatic compounds have been developed by utilizing Ir‐mediated CH bond activation of ethylene‐ or ethylidene‐bridged diphenol derivatives. Depending on the bridging alkyl groups, two types of iridaoxabenzenes, both of which are doubly fused with benzo and benzofuran units, have been obtained. Studies on their structures and electronic characters indicate that both complexes have an aromatic character on the iridaoxacycles, and their π‐conjugated systems are fully delocalized over the whole molecular skeletons. These novel metallaaromatic complexes exhibited some reactivities which are distinct from those reported for the non‐fused metallaaromatic compounds.

    DOI: 10.1002/asia.202300640

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  • Binuclear Complexes Supported by a Tetrapyridyl Ligand with a Bending Anthraquinodimethane Linker

    Takahiro Iwamoto, Yuta Sotome, Youichi Ishii

    ACS Organic & Inorganic Au   2023.8

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    Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acsorginorgau.3c00021

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  • Retro-Vinylidene Rearrangements of P- and S-Substituted Ruthenium Vinylidene Complexes Reviewed

    T. Iwamoto, K. Saito, T. Mitsubo, T. Kuwabara, Y. Ishii

    Organometallics   42 ( 2 )   167 - 173   2023.1

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.organomet.2c00552

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  • Vinylidene Complexes

    Takahiro Iwamoto, Youichi Ishii

    Encyclopedia of Inorganic and Bioinorganic Chemistry   1 - 14   2022.6

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  • Experimental Observation of β-Carbon Elimination from Alkenylrhodium Complexes through Exchange Reactions of the Alkenyl Unit

    Takahiro Iwamoto, Koushi Shibuya, Tomoyuki Takakuwa, Takuya Kuwabara, Youichi Ishii

    Organometallics   41 ( 3 )   182 - 186   2022.2

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    Authorship:Lead author   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.organomet.1c00695

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  • Development of P- and N-Chirogenic Ligands Based on Chiral Induction from a Phosphorus Donor to a Nitrogen Donor in Palladium Complexes Reviewed

    Takahiro Iwamoto, Yoshiyuki Mizuhata, Norihiro Tokitoh, Masaharu Nakamura

    Organometallics   39 ( 10 )   1672 - 1677   2020.5

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    Authorship:Lead author, Corresponding author   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.organomet.0c00154

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  • Iron-catalysed enantioselective Suzuki–Miyaura coupling of racemic alkyl bromides Reviewed

    Iwamoto, T, Okuzono, C, Adak, L, Jin, M, Nakamura, M

    Chem. Commun   55   1128 - 1131   2019

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    DOI: 10.1039/c8cc09523j

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  • Endergonic addition of N-methylamines to aromatic ketones driven by photochemical offset of the entropic cost Reviewed

    Takahiro Iwamoto, Atsushi Hosokawa, Masaharu Nakamura

    Chemical Communication   55   11683 - 11686   2019

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  • Iron-Catalyzed Cross Coupling of Aryl Chlorides with Alkyl Grignard Reagents: Synthetic Scope and FeII/FeIV Mechanism Supported by X-ray Absorption Spectroscopy and Density Functional Theory Calculations Reviewed

    Agata, R, Takaya, H, Matsuda, H, Nakatani, N, Takeuchi, K, Iwamoto, T, Hatakeyama, T, Nakamura, M

    Bull. Chem. Soc. Jpn.   92 ( 2 )   381 - 390   2019

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:CHEMICAL SOC JAPAN  

    A combination of iron(III) fluoride and 1,3-bis(2,6-diiso-propylphenyl) imidazolin-2-ylidene (SIPr) catalyzes the high-yielding cross coupling of an electron-rich aryl chloride with an alkyl Grignard reagent, which cannot be attained using other iron catalysts. A variety of alkoxy-or amino-substituted aryl chlorides can be cross-coupled with various alkyl Grignard reagents regardless of the presence or absence of beta-hydrogens in the alkyl group. A radical probe experiment using 1-(but-3-enyl)- 2-chlorobenzene does not afford the corresponding cyclization product, therefore excluding the intermediacy of radical species. Solution-phase X-ray absorption spectroscopy (XAS) analysis, with the help of density functional theory (DFT) calculations, indicates the formation of a high-spin (S = 2) heteroleptic difluorido organoferrate(II), [MgX][(FeF2)-F-II(SIPr)-(Me/alkyl)], in the reaction mixture. DFT calculations also support a feasible reaction pathway, including the formation of a difluorido organoferrate(II) intermediate which undergoes a novel Lewis acid-assisted oxidative addition to form a neutral organoiron(IV) intermediate, which leads to an Fe-II/Fe-IV catalytic cycle, where the fluorido ligand and the magnesium ion play key roles.

    DOI: 10.1246/bcsj.20180333

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  • DFT and AFIR Study on the Mechanism and the Origin of Enantioselectivity in Iron-Catalyzed Cross-Coupling Reactions Reviewed

    Akhilesh K. Sharma, W. M. C. Sameera, Masayoshi Jin, Laksmikanta Adak, Chiemi Okuzono, Takahiro Iwamoto, Masako Kato, Masaharu Nakamura, Keiji Morokuma

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   139 ( 45 )   16117 - 16125   2017.11

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

    The mechanism of the full catalytic cycle for Fe-chiral-bisphosphine-catalyzed cross-coupling reaction between alkyl halides and Grignard reagents (Nakamura and co-workers, J. Am. Chem. Soc. 2015, 137, 7128) was rationalized by using density functional theory (DFT) and multicomponent artificial force-induced reaction (MC-AFIR) methods. The computed mechanism consists of (a) C-Cl activation, (b) transmetalation, (c) C-Fe bond formation, and (d) C-C bond formation through reductive elimination. Our survey on the prereactant complexes suggested that formation of Fe-II(BenzP*)Ph-2 and Fe-I(BenzP*)Ph complexes are thermodynamically feasible. Fe-I(BenzP*)Cl complex is the active intermediate for C-Cl activation. Fe-II(BenzP*)Ph-2 complex can be formed if the concentration of Grignard reagent is high. However, it leads to biphenyl (byproduct) instead of the cross-coupling product. This explains why slow addition of Grignard reagent is critical for the cross-coupling reaction. The MC-AFIR method was used for systematic determination of transition states for C-Fe bond formation and C-C bond formation starting from the key intermediate Fe-II(BenzP*)PhCl. According to our detailed analysis, C-C bond formation is the selectivity-determining step. The computed enantiomeric ratio of 95:5 is in good agreement with the experimental ratio (90:10). Energy decomposition analysis suggested that the origin of the enantioselectivity is the deformation of Ph-ligand in Fe-complex, which is induced by the bulky tert-butyl group of BenzP* ligand. Our study provides important mechanistic insights for the cross-coupling reaction between alkyl halides and Grignard reagents and guides the design of efficient Fe-based catalysts for cross-coupling reactions.

    DOI: 10.1021/jacs.7b05917

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    Other Link: http://orcid.org/0000-0002-2349-0714

  • Iron-Catalyzed anti-Selective Carbosilylation of Internal Alkynes Reviewed

    Takahiro Iwamoto, Tatsushi Nishikori, Naohisa Nakagawa, Hikaru Takaya, Masaharu Nakamura

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   56 ( 43 )   13298 - 13301   2017.10

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    Authorship:Lead author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    Reported is the anti-selective carbosilylation of internal alkynes with silylborane and alkyl halides using a FeBr2/DPPE catalyst system. The iron catalyst allows simultaneous introduction of a carbon electrophile and a silicon nucleophile to simple internal alkynes, including diaryl-, dialkyl-, and aryl/alkyl-substituted alkynes, in a highly stereoselective manner. Alkyl halides are applicable as the electrophiles, thereby enabling the synthesis of a variety of tetrasubstituted alkenylsilanes. In addition, syn-selective carbosilylation was achieved through stereoswitching, by using a silylborane having oxygen functionality on the silyl group. This novel iron-catalyzed carbosilylation is a useful tool for expedient synthesis of stereodefined multisubstituted olefins, a fundamental structural motif in organic chemistry.

    DOI: 10.1002/anie.201706333

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  • Shortest Double-Walled Carbon Nanotubes Composed of Cycloparaphenylenes Reviewed

    Sigma Hashimoto, Takahiro Iwamoto, Daisuke Kurachi, Eiichi Kayahara, Shigeru Yamago

    CHEMPLUSCHEM   82 ( 7 )   1015 - 1020   2017.7

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    The host-guest chemistry of cycloparaphenylenes (CPPs) of different sizes is described. [n]CPPs (n= 5, 6, 7, 8, and 10) selectively interact with [n+5] CPPs, forming complexes [n+5] CPP superset of[n]CPP, which are the shortest double-walled armchair carbon nanotubes. The size selectivity is dictated by the difference in diameters of the CPPs (that is, 0.34-0.35 nm), which maximizes attractive van der Waals interactions. Theoretical calculations suggest that the orbital energies of the CPPs become perturbed upon complex formation, and orbital mixing between the two CPPs is predicted for large CPP pairs. The association constants in 1,1,2,2-[D-2] tetrachloroethane, estimated by H-1 NMR titration, are approximately 103 molL(- 1) at 508 degrees C. Van't Hoff plot analysis reveals that complexation is driven mainly by entropy owing to desolvation of the CPPs. [13] CPP also forms a complex with [4] cyclo-2,7-pyrenylene ([4] CPY), which is a p-extended [8]CPP. Theoretical calculations suggest that the formation of [13]CPP superset of [4]CPY is more exothermic than that of [13] CPP superset of[8]CPP. A ternary complex, [15] CPP superset of [10]CPP superset of C60, is also formed by mixing [15]CPP and [10]CPP superset of C60.

    DOI: 10.1002/cplu.201700097

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  • Shortest Double-Walled Carbon Nanotubes Composed of Cycloparaphenylenes Reviewed

    Sigma Hashimoto, Takahiro Iwamoto, Daisuke Kurachi, Eiichi Kayahara, Shigeru Yamago

    CHEMPLUSCHEM   82 ( 7 )   942 - 942   2017.7

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    Language:English   Publisher:WILEY-V C H VERLAG GMBH  

    Invited for this month's cover is the group of Prof. Dr. Shigeru Yamago at the Kyoto University (Japan). The image shows the host-guest possibilities of cycloparaphenylenes (CPPs) of different sizes. Size selective interaction between [n]CPP and [n+5]CPP affords a host-guest complex, [n+5]CPP superset of[n]CPP, which is the shortest double-walled armchair carbon nanotube. The size-selective complex formation illustrates the importance of van der Waals interactions. A ternary complex, [15]CPP superset of[10]CPP superset of C-60, also forms from [15]CPP, [10]CPP, and C60.

    DOI: 10.1002/cplu.201700263

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  • ONO-pincer ruthenium complex-bound norvaline for efficient catalytic oxidation of methoxybenzenes with hydrogen peroxide Reviewed

    Ryota Yoshida, Katsuhiro Isozaki, Tomoya Yokoi, Nobuhiro Yasuda, Koichiro Sadakane, Takahiro Iwamoto, Hikaru Takaya, Masaharu Nakamura

    ORGANIC & BIOMOLECULAR CHEMISTRY   14 ( 31 )   7468 - 7479   2016

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:ROYAL SOC CHEMISTRY  

    The enhanced catalytic activity of ruthenium complex-bound norvaline Boc-L-[Ru]Nva-OMe 1, in which the ONO-pincer ruthenium complex Ru(pydc)(terpy) 2 is tethered to the alpha-side chain of norvaline, has been demonstrated for the oxidation of methoxybenzenes to p-benzoquinones with a wide scope of substrates and unique chemoselectivity.

    DOI: 10.1039/c6ob00969g

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  • Ligand-Controlled Synthesis of [3]- and [4]Cyclo-9,9-dimethyl-2,7-fluorenes through Triangle- and Square-Shaped Platinum Intermediates Reviewed

    Eiichi Kayahara, Rui Qu, Mitsuru Kojima, Takahiro Iwamoto, Toshiyasu Suzuki, Shigeru Yamago

    CHEMISTRY-A EUROPEAN JOURNAL   21 ( 52 )   18939 - 18943   2015.12

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    The syntheses of [3]-and [4] cyclo-9,9-dimethyl-2,7-fluorenes ([3] and [4] CFRs), cyclic trimer, and tetramers of 9,9-dimethyl-2,7-fluorene (FR), respectively, were achieved by the platinum-mediated assembly of FR units and subsequent reductive elimination of platinum. A triangle-shaped tris-platinum complex and a square-shaped tetra-platinum complex were obtained by changing the platinum ligand. The structure of the triangle complex was unambiguously determined by X-ray crystallographic analysis. Reductive elimination of each complex gave [3] and [4] CFRs. Two rotamers of [3] CFR were sufficiently stable at room temperature and were separated by chromatography. The physical properties of the CFRs were also investigated theoretically and experimentally.

    DOI: 10.1002/chem.201504369

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  • Radical Ions of Cyclopyrenylene: Comparison of Spectral Properties with Cycloparaphenylene Reviewed

    Mamoru Fujitsuka, Sachiko Tojo, Takahiro Iwamoto, Eiichi Kayahara, Shigeru Yamago, Tetsuro Majima

    JOURNAL OF PHYSICAL CHEMISTRY A   119 ( 18 )   4136 - 4141   2015.5

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

    Hoop-shaped pi-conjugated molecules have attracted much attention. In this study, the radical ions of [4]cyclo-2,7-pyrenylene ([4]CPY), a cyclic tetramer of pyrene, and [4]cyclo-4,5,9,10-tetrahydro-2,7-pyrenylene ([4]CHPY) were investigated using radiation chemical methods, namely, gamma-ray radiolysis and pulse radiolysis. The absorption spectra of the radical ions of [4]CPY and [4]CHPY showed clear peaks in the near-IR and UV-vis regions similar to those of [8]cycloparaphenylene ([8]CPP). Theoretical calculations using time-dependent density functional theory provided reasonable assignments of the observed absorption bands. It was indicated that the C4-C5 and C9-C10 ethylene bonds of [4]CHPY do not contribute to the electronic transitions, resulting in absorption spectra similar to those of [8]CPP. On the other hand, it was confirmed that the allowed electronic transitions of the radical ions of [4]CPY are different from those of the radical ions of [4]CHPY and [8]CPP.

    DOI: 10.1021/acs.jpca.5b01189

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  • Investigation of organoiron catalysis in Kumada-Tamao-Corriu-type cross-coupling reaction assisted by solution-phase X-ray absorption spectroscopy Reviewed

    Takaya, H., Nakajima, S., Nakagawa, N., Isozaki, K., Iwamoto, T., Imayoshi, R., Gower, N.J., Adak, L., Hatakeyama, T., Honma, T., Takagaki, M., Sunada, Y., Nagashima, H., Hashizume, D., Takahashi, O., Nakamura, M.

    Bulletin of the Chemical Society of Japan   88 ( 3 )   410 - 418   2015

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1246/bcsj.20140376

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  • Iron fluoride/N-heterocyclic carbene catalyzed cross coupling between deactivated aryl chlorides and alkyl grignard reagents with or without β-hydrogens Reviewed

    Agata, R., Iwamoto, T., Nakagawa, N., Isozaki, K., Hatakeyama, T., Takaya, H., Nakamura, M.

    Synthesis (Germany)   47 ( 12 )   1733 - 1740   2015

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1055/s-0034-1380361

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  • Partial Charge Transfer in the Shortest Possible Metallofullerene Peapod, La@C-82 subset of[11]Cycloparaphenylene Reviewed

    Takahiro Iwamoto, Zdenek Slanina, Naomi Mizorogi, Jingdong Guo, Takeshi Akasaka, Shigeru Nagase, Hikaru Takaya, Nobuhiro Yasuda, Tatsuhisa Kato, Shigeru Yamago

    CHEMISTRY-A EUROPEAN JOURNAL   20 ( 44 )   14403 - 14409   2014.10

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    Authorship:Lead author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    [11]Cycloparaphenylene ([11]CPP) selectively encapsulates La@C-82 to form the shortest possible metallofullerene-carbon nanotube (CNT) peapod, La@C-82< subset of>[11]CPP, in solution and in the solid state. Complexation in solution was affected by the polarity of the solvent and was 16times stronger in the polar solvent nitrobenzene than in the nonpolar solvent 1,2-dichlorobenzene. Electrochemical analysis revealed that the redox potentials of La@C-82 were negatively shifted upon complexation from free La@C-82. Furthermore, the shifts in the redox potentials increased with polarity of the solvent. These results are consistent with formation of a polar complex, (La@C-82)(-)< subset of>[11]CPP+, by partial electron transfer from [11]CPP to La@C-82. This is the first observation of such an electronic interaction between a fullerene pea and CPP pod. Theoretical calculations also supported partial charge transfer (0.07) from [11]CPP to La@C-82. The structure of the complex was unambiguously determined by X-ray crystallographic analysis, which showed the La atom inside the C-82 near the periphery of the [11]CPP. The dipole moment of La@C-82 was projected toward the CPP pea, nearly perpendicular to the CPP axis. The position of the La atom and the direction of the dipole moment in La@C-82< subset of>[11]CPP were significantly different from those observed in La@C-82< subset of>CNT, thus indicating a difference in orientation of the fullerene peas between fullerene-CPP and fullerene-CNT peapods. These results highlight the importance of pea-pea interactions in determining the orientation of the metallofullerene in metallofullerene-CNT peapods.

    DOI: 10.1002/chem.201403879

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  • New Organic Chemistry of Three-Dimensional pi-Conjugated Compounds Reviewed

    Shigeru Yamago, Eiichi Kayahara, Takahiro Iwamoto

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   72 ( 9 )   992 - 1005   2014.9

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    Language:Japanese   Publisher:SOC SYNTHETIC ORGANIC CHEM JPN  

    This article describes the most recent developments in the synthesis of three dimensional (3D) pi-conjugated molecules and the elucidation of their properties accomplished by the authors' group. Cycloparaphenylenes (CPPs) of different sizes and a cage-like 3D molecule were synthesized based on the platinum-mediated assembly of pi c-units and subsequent reductive elimination of platinum. The assembly of pi c-units mimics the self-assembly process for the formation of supra-molecular transition metal-ligand complexes with 3D cages and polyhedral structures. Furthermore, reductive elimination of platinum successfully took place with high efficiency, despite the high strain energy of the target molecule. Several size-dependent properties of CPPs, namely the photophysical, redox, and host-guest chemistries, were also clarified. These results are of use for a molecular-level understanding of CNT physical properties as well as fullerene peapods. Theoretical and electrochemical studies suggest that small CPPs and their derivatives should be excellent lead compounds for molecular electronics.

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  • Properties of Sizeable [n]Cycloparaphenylenes as Molecular Models of Single-Wall Carbon Nanotubes Elucidated by Raman Spectroscopy: Structural and Electron-Transfer Responses under Mechanical Stress Reviewed

    Miriam Pena Alvarez, Paula Mayorga Burrezo, Miklos Kertesz, Takahiro Iwamoto, Shigeru Yamago, Jianlong Xia, Ramesh Jasti, Juan T. Lopez Navarrete, Mercedes Taravillo, Valentin G. Baonza, Juan Casado

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   53 ( 27 )   7033 - 7037   2014.7

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    [n]Cycloparaphenylenes behave as molecular templates of "perfectly chemically defined" single-wall carbon nanotubes. These [n]CPP molecules have electronic, mechanical, and chemical properties in size correspondence with their giant congeners. Under mechanical stress, they form charge-transfer salts, or complexes with fullerene, by one-electron concave-convex electron transfer.

    DOI: 10.1002/anie.201400719

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  • Radical Ions of Cycloparaphenylenes: Size Dependence Contrary to the Neutral Molecules Reviewed

    Mamoru Fujitsuka, Sachiko Tojo, Takahiro Iwamoto, Eiichi Kayahara, Shigeru Yamago, Tetsuro Majima

    JOURNAL OF PHYSICAL CHEMISTRY LETTERS   5 ( 13 )   2302 - 2305   2014.7

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

    Cycloparaphenylenes (CPPs) have attracted wide attention because of their interesting properties owing to distorted and strained aromatic systems and radially oriented p orbitals. For application of CPPs, information on their charged states (radical cation and radical anion) is essential. Here, we measured absorption spectra of the radical cations and the radical anions of CPPs with various ring sizes over a wide spectral region by means of radiation chemical methods. The peak position of the near-IR bands for both the radical cation and the radical anion shifted to lower energies with an increase in the ring size. This trend is contrary to what is observed for transitions between the HOMO and LUMO of the neutral CPP. The observed spectra of the CPP radical ions were reasonably assigned based on time-dependent density functional theory. These results indicate that the next HOMO and the next LUMO levels are important in the electronic transitions of radical ions.

    DOI: 10.1021/jz5009054

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  • Properties of Triplet-Excited [n]Cycloparaphenylenes (n=8-12): Excitation Energies Lower than Those of Linear Oligomers and Polymers Reviewed

    Mamoru Fujitsuka, Chao Lu, Takahiro Iwamoto, Eiichi Kayahara, Shigeru Yamago, Tetsuro Majima

    JOURNAL OF PHYSICAL CHEMISTRY A   118 ( 25 )   4527 - 4532   2014.6

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

    Cycloparaphenylenes (CPPs), a class of hoop-shaped conjugated macrocycles, have attracted the attention of researchers in various fields because of their interesting properties. Although their properties in the singlet-excited state have been reported, there is no systematic information on the triplet-excited state. In the present study, the properties of triplet-excited [n]CPP (n = 8-12, where n denotes the number of phenyl rings) were comprehensively investigated. The phosphorescence peak shifted to the shorter-wavelength side with increasing ring size of the CPPs, indicating smaller triplet energy for smaller CPPs. It was found that the triplet energy of a smaller CPP is even smaller than those of poly(p-phenylene)s, indicating that small hoop-shaped conjugated macrocycles are effective in realizing low-band gap materials. By applying laser flash photolysis, the T-n-T-1 absorption spectra of CPPs were obtained, from which the size-dependence of energy levels of higher triplet states were also determined. Generation of singlet oxygen by the energy transfer from a triplet-excited CPP was confirmed. The generation yield became smaller with increasing size of the CPP in accordance with the triplet yield. From these observations, the size-dependence of the deactivation pathways is explained.

    DOI: 10.1021/jp504689q

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  • Synthesis, Characterization, and Properties of [4]Cyclo-2,7-pyrenylene: Effects of Cyclic Structure on the Electronic Properties of Pyrene Oligomers Reviewed

    Takahiro Iwamoto, Eiichi Kayahara, Nobuhiro Yasuda, Toshiyasu Suzuki, Shigeru Yamago

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   53 ( 25 )   6430 - 6434   2014.6

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    A cyclic tetramer of pyrene, [4]cyclo-2,7-pyrenylene ([4]CPY), was synthesized from pyrene in six steps and 18% overall yield by the platinum-mediated assembly of pyrene units and subsequent reductive elimination of platinum. The structures of the two key intermediates were unambiguously determined by X-ray crystallographic analysis. DFT calculations showed that the topology of the frontier orbitals in [4]CPY was essentially the same as those in [8]cycloparaphenylene ([8]CPP), and that all the pyrene units were fully conjugated. The electrochemical analyses proved the electronic properties of [4]CPY to be similar to those of [8]CPP. The results are in sharp contrast to those obtained for the corresponding linear oligomers of pyrene in which each pyrene unit was electronically isolated. The results clearly show a novel effect of the cyclic structure on cyclic pi-conjugated molecules.

    DOI: 10.1002/anie.201403624

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  • Electron Transfer in a Supramolecular Associate of a Fullerene Fragment Reviewed

    Maria Gallego, Joaquin Calbo, Juan Arago, Rafael M. Krick Calderon, Fernando H. Liquido, Takahiro Iwamoto, Allison K. Greene, Edward A. Jackson, Emilio M. Perez, Enrique Orti, Dirk M. Guldi, Lawrence T. Scott, Nazario Martin

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   53 ( 8 )   2170 - 2175   2014.2

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    Herein, we investigate the association of a fullerene fragment, hemifullerene C30H12, with an electron-donating bowl-shaped tetrathiafulvalene derivative (truxTTF). UV/Vis titrations and DFT calculations support formation of the supramolecular complex, for which an association constant of log K-a=3.6 +/- 0.3 in CHCl3 at room temperature is calculated. Remarkably, electron transfer from truxTTF to C30H12 to form the fully charge-separated species takes place upon irradiation of the associate with light, constituting the first example in which a fullerene fragment mimics the electron-accepting behavior of fullerenes within a supramolecular complex.

    DOI: 10.1002/anie.201309672

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  • Organoplatinum-Mediated Synthesis of Cyclic pi-Conjugated Molecules: Towards a New Era of Three-Dimensional Aromatic Compounds Reviewed

    Shigeru Yamago, Eiichi Kayahara, Takahiro Iwamoto

    CHEMICAL RECORD   14 ( 1 )   84 - 100   2014.2

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

    This article describes the most recent developments in the synthesis of three-dimensional -conjugated molecules and the elucidation of their properties made by our research group. Various cycloparaphenylenes (CPPs) of different sizes and a cage-like 3D molecule were synthesized based on the platinum-mediated assembly of -units and subsequent reductive elimination of platinum. The assembly of -units by this method mimics the self-assembly process for the formation of supramolecular ligand-metal complexes with 3D cages and polyhedral structures. Furthermore, reductive elimination of platinum successfully took place with high efficiency, despite the high strain energy of the target molecule. Several size-dependent physical properties of CPPs, namely the photophysical, redox, and host-guest chemistries, were also clarified. These results are of use for a molecular-level understanding of CNT physical properties as well as fullerene peapods. Theoretical and electrochemical studies suggest that small CPPs and their derivatives should be excellent lead compounds for molecular electronics.

    DOI: 10.1002/tcr.201300035

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  • 三次元状n共役分子の新しい有機化学 Reviewed

    山子 茂, 茅原 栄一, 岩本 貴寛

    有機合成化学協会誌   69   992 - 1005   2014

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  • Chameleon-like behaviour of cyclo[n] paraphenylenes in complexes with C-70: on their impressive electronic and structural adaptability as probed by Raman spectroscopy Reviewed

    Miriam Pena Alvarez, Paula Mayorga Burrezo, Takahiro Iwamoto, Lili Qiu, Miklos Kertesz, Mercedes Taravillo, Valentin G. Baonza, Juan T. Lopez Navarrete, Shigeru Yamago, Juan Casado

    FARADAY DISCUSSIONS   173   157 - 171   2014

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    A series of four 1: 1 host guest supramolecular complexes of [n]CPPs and C-70 have been analyzed by Raman spectroscopy in the solid state and complemented with the analysis of their spectroscopic responses under mechanical and thermal stresses. By following the frequency behaviour of the G and RBM modes we have found that [10]CPP in the [10] CPP@C-70 complex displays a more "ordered" structure. However, in [11]CPP@C-70, the nanoring becomes oval-shaped with closer contacts with the C-70 poles and less conformational restriction in the flattened region. By mechanical and thermal stresses we are able to modify the lying conformation of [10]CPP@C-70 towards a standing orientation. [11]CPP@C-70 resists pressure changes, although it tends to shift from the standing to the lying orientation by heating. As for the crystal cell, the [n]CPPs occupy the residual empty spaces while the main crystallographic positions are reserved for. These are new examples of the impressive adaptability of the [n]CPP molecules to different physico-chemical environments, a chameleon-like property which reveals the delicate equilibrium provided by cyclic conjugation and ring strain.

    DOI: 10.1039/c4fd00103f

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  • Synthesis and physical properties of a ball-like three-dimensional pi-conjugated molecule Reviewed

    Eiichi Kayahara, Takahiro Iwamoto, Hikaru Takaya, Toshiyasu Suzuki, Mamoru Fujitsuka, Tetsuro Majima, Nobuhiro Yasuda, Naoto Matsuyama, Shu Seki, Shigeru Yamago

    NATURE COMMUNICATIONS   4   2013.10

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    Curved pi-conjugated molecules with closed and three-dimensional (3D) structures, such as fullerenes and carbon nanotubes, have been the subject of intensive research due to their potential applications in molecular electronics. However, basic molecular skeletons of 3D molecules are limited because of the lack of a rational and selective synthetic method by organic synthesis. Here we report the synthesis of a 3D pi-conjugated molecule based on the platinum-mediated assembly of four molecules of a stannylated trisubstituted benzene derivative forming a hexanuclear platinum complex with an octahedral shape, from which reductive elimination of platinum gave the target molecule. As many supramolecular transition metal-ligand complexes with 3D cages and polyhedral structures have been synthesized by self-assembly of ligands and metals, the current assembly/reductive elimination strategy could provide a variety of new 3D pi-conjugated molecules with different structures and topologies, which are challenging to obtain using conventional synthetic methods.

    DOI: 10.1038/ncomms3694

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  • Enhancement of the Quinoidal Character for Smaller [n]Cycloparaphenylenes Probed by Raman Spectroscopy Reviewed

    Mamoru Fujitsuka, Takahiro Iwamoto, Eiichi Kayahara, Shigeru Yamago, Tetsuro Majima

    CHEMPHYSCHEM   14 ( 8 )   1570 - 1572   2013.6

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    DOI: 10.1002/cphc.201300144

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  • Syntheses and properties of cycloparaphenylenes and their derivatives Reviewed

    Yamago Shigeru, Kayahara Eiichi, Iwamoto Takahiro

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   245   2013.4

  • Selective synthesis of [6]-, [8]-, and [10]cycloparaphenylenes Reviewed

    Eiichi Kayahara, Takahiro Iwamoto, Toshiyasu Suzuki, Shigeru Yamago

    Chemistry Letters   42 ( 6 )   621 - 623   2013

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    The selective synthesis of [6]-, [8]-, and [10]cycloparaphenylenes (CPPs) was achieved by a new synthetic route involving Ni(0)-mediated coupling of bis(para-haloaryl)dinuclear arylplatinum complexes and the reductive elimination of the complexes. Importantly, the highly strained [6]CPP was prepared in good overall yield. © 2013 The Chemical Society of Japan.

    DOI: 10.1246/cl.130188

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  • Size- and orientation-selective encapsulation of C70 by cycloparaphenylenes Reviewed

    Takahiro Iwamoto, Yoshiki Watanabe, Hikaru Takaya, Takeharu Haino, Nobuhiro Yasuda, Shigeru Yamago

    Chemistry - A European Journal   19 ( 42 )   14061 - 14068   2013

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    The size- and orientation-selective formation of the shortest-possible C70 peapod in solution and in the solid state by using the shortest structural unit of an "armchair" carbon nanotube (CNT), cycloparaphenylene (CPP), has been studied. [10]CPP and [11]CPP exothermically formed 1:1 complexes with C70, thereby giving the resulting peapods. A van't Hoff plot analysis revealed that the formation of these complexes in 1, 2-dichlorobenzene was mainly driven by entropy, whereas the theoretical calculations suggested that the formation of the complex in the gas phase was predominantly driven by enthalpy. C70 was found to exist in two distinct orientations inside the CPP cavity, namely "lying" and "standing", depending on the specific size of the CPP. The theoretical calculations and the X-ray crystallographic analysis revealed that the interactions between [10]CPP and the short axis of C70 in its lying orientation were isotrop-ic and similar to those observed between [10]CPP and C60. However, the interactions between [11]CPP and C70 in its standing orientation were aniso-tropic, thereby involving the radial deformation of [11]CPP into an ellipsoidal shape. This "induced fit" maximized the van der Waals interactions with the long axis of C70. Theoretical calculations revealed that the deformation occurred readily with low energy loss, thus suggesting that CPPs are highly radially elastic molecules. These results also indicate that the same type of radial deformation should occur in CNT peapods that encapsulate aniso-tropic fullerenes. © 2013 Wiley-VCH Verlag GmbH &amp
    Co. KGaA.

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  • Size-dependent fluorescence properties of [n]cycloparaphenylenes (n=8-13), hoop-shaped pi-conjugated molecules Reviewed

    Mamoru Fujitsuka, Dae Won Cho, Takahiro Iwamoto, Shigeru Yamago, Tetsuro Majima

    PHYSICAL CHEMISTRY CHEMICAL PHYSICS   14 ( 42 )   14585 - 14588   2012

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    Hoop-shaped pi-conjugated molecules such as cycloparaphenylene (CPP) have attracted the attention of many chemists because they exhibit interesting properties due to the distorted pi-electron system. To gain a systematic understanding of the properties that result from distorted pi-electron systems, it is important to know precisely how these properties depend on the hoop size. In the present study, we have investigated the size dependence of the fluorescence properties of CPPs. The fluorescence spectra of smaller CPPs showed red-shifted fluorescence peaks, smaller fluorescence quantum yields, and longer lifetimes, when compared to those of larger ones. One of the important factors that gave rise to these fluorescence properties of smaller CPPs was greater structural relaxation from the Franck-Condon state, which is a postulation supported by theoretical calculations. The structural relaxation in the picosecond domain was experimentally detected by the fluorescence upconversion method. The present results are an important example that confirms steric factors strongly governing the fluorescence properties of a molecule.

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  • Selective and Random Syntheses of [n]Cycloparaphenylenes (n=8-13) and Size Dependence of Their Electronic Properties Reviewed

    Takahiro Iwamoto, Yoshiki Watanabe, Youichi Sakamoto, Toshiyasu Suzuki, Shigeru Yamago

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   133 ( 21 )   8354 - 8361   2011.6

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    [n]Cycloparaphenylenes (n = 8-13, CPPs) were synthesized, and their physical properties were systematically investigated. [8] and [12]CPPs were selectively prepared from the reaction of 4,4'-bis(trimethylstannyl)biphenyl and 4,4 ''-bis(trimethylstannyl)terphenyl, respectively, with Pt(cod)Cl-2 (cod = 1,5-cyclooctadiene) through square-shaped tetranuclear platinum intermediates. A mixture of [8]-[13]CPPs was prepared in good combined yields by mixing biphenyl and terphenyl precursors with platinum sources. Products were easily separated and purified by using gel permeation chromatography. In H-1 NMR spectra, the proton of the CPPs shifts to a lower field as n increased due to an anisotropic effect from the nearby PP moieties. Although the UV-vis spectra were rather insensitive to the size of the CPPs, the fluorescence spectra changed significantly in relation to their size. A larger Stokes shift was observed for the smaller CPPs. Redox properties of the CPPs were measured for the first time by using cyclic voltammetry, and the smaller CPPs had lower oxidation potentials. The results are consistent with the HOMO energies of CPPs, of which the smaller CPPs had higher energies.

    DOI: 10.1021/ja2020668

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  • Size-Selective Encapsulation of C-60 by [10]Cycloparaphenylene: Formation of the Shortest Fullerene-Peapod Reviewed

    Takahiro Iwamoto, Yoshiki Watanabe, Tatsuya Sadahiro, Takeharu Haino, Shigeru Yamago

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   50 ( 36 )   8342 - 8344   2011

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    DOI: 10.1002/anie.201102302

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  • Size-Selective Encapsulation of C60 by [10]Cycloparaphenylene. Formation of the Shortest Fullerene-Peapod Reviewed

    Iwamoto, T, Watanabe, Y, Sadahiro, T, Haino, T, Yamago, S

    Angew. Chem. Int. Ed.   32   1576 - 1582   2011

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  • Synthesis of [8]Cycloparaphenylene from a Square-Shaped Tetranuclear Platinum Complex Reviewed

    Shigeru Yamago, Yoshiki Watanabe, Takahiro Iwamoto

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   49 ( 4 )   757 - 759   2010

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    DOI: 10.1002/anie.200905659

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  • Mechanistic Study on C-H Activation Reactions with Low-Valent Cobalt Catalysts

    吉戒直彦, LEE Pin Sheng, XU Wengang, 中村正治, 岩本貴寛, 磯崎勝弘, 仲嶋翔, 吉田亮太, 高谷光

    SPring-8/SACLA利用研究成果集(Web)   8 ( 3 )   2020

  • Metalated Amino Acids and Peptides: A Key Functional Platform for Applications to Controlled Metal Array Fabrication and Supramolecular Catalysts Reviewed

    高谷光, 磯崎勝弘, 吉田亮太, 吉田亮太, 横井友哉, 横井友哉, 尾形和樹, 尾形和樹, 社納貴文, 社納貴文, 安田伸広, 岩本貴寛, 岩本貴寛, 中村正治

    有機合成化学協会誌   76 ( 10 )   1010 - 1023   2019

  • 光触媒が拓く炭素資源の分子変換-二酸化炭素の一電子還元を起点とするカルボキシル化反応

    細川敦, 岩本 貴寛, 中村正治

    化学   73   70 - 71   2018

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  • 鉄触媒不斉カップリング反応を用いたα-アリールプロピオン酸誘導体の立体選択的合成

    奥園智絵美, 奥園智絵美, 岩本貴寛, 岩本貴寛, 岩本貴寛, ADAK Laksmikanta, ADAK Laksmikanta, 神将吉, 高谷光, 高谷光, 中村正治, 中村正治

    日本化学会春季年会講演予稿集(CD-ROM)   97th   2017

  • Application of solution-phase XAFS for homogeneous catalyst: mechanistic study on iron-catalyzed cross-coupling reactions

    Takaya Hikaru, Nakajima Sho, Iwamoto Takahiro, Aoki Yuma, Agata Ryosuke, Suzuki Tsuyoshi, Isozaki Katsuhiro, Sunada Yusuke, Takagaki Masafumi, Honnma Tetsuo, Nagashima Hideo, Nakamura Masaharu

    Proceeding of Annual/Fall Meetings of the Japan Petroleum Institute   2016 ( 0 )   201‐202 - 146   2016.11

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    放射光X線を用いるX線吸収分光(XAFS)の普及と量子科学計算をベースとしたXAFSシミュレーションに進歩によって、均一系分子触媒の溶液構造の精密構造解析を有機化学者が自らの手で手軽に行えるようになってきた。本講演では、常磁性のためNMR分析が困難な常磁性鉄錯体を用いる均一系触媒反応の機構研究において、溶液XAFSが極めて強力な手段となり、反応溶液中の触媒中間体の同定・構造決定に基づく精密な反応機構の決定が可能となることを紹介したい。

    DOI: 10.11523/sekiyu.2016f.0_146

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  • 放射光X線吸収分光による鉄触媒の溶液構造解析

    高谷光, 仲嶋翔, 岩本貴寛, 岩本貴寛, 青木雄真, 縣亮介, 磯崎勝弘, 砂田祐輔, 高垣昌史, 本間徹生, 永島英夫, 永島英夫, 中村正治

    触媒討論会討論会A予稿集   118th   470   2016.9

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  • サイズの異なるシクロパラフェニレン間のホスト‐ゲスト化学

    橋本士雄磨, 岩本貴寛, 倉知大介, 河野太郎, 茅原栄一, 山子茂

    基礎有機化学討論会要旨集   27th   35   2016.9

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  • シクロパラフェニレンの酸化特性の解明

    橋本士雄磨, 岩本貴寛, 倉知大介, 河野太郎, 茅原栄一, 山子茂

    第25回基礎有機化学討論会   2016.9

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  • 放射光で観る分子性錯体の溶液中分子構造と触媒作用

    高谷光, 仲嶋翔, 岩本貴寛, 岩本貴寛, 青木雄真, 縣亮介, 磯崎勝弘, 本間徹生, 高垣昌史, 為則雄祐, 永島英夫, 永島英夫, 砂田祐輔, 中村正治

    錯体化学会討論会講演要旨集   66th   370   2016.8

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  • フェニル鉄中間体の溶液構造解析に基づく鉄触媒クロスカップリング反応の機構研究

    仲嶋翔, 高谷光, 磯崎勝弘, 磯崎勝弘, 岩本貴寛, 岩本貴寛, 中川尚久, GOWER N.J, 今吉隆治, 本間徹生, 高垣昌史, 砂田祐輔, 永島英夫, 永島英夫, 畠山琢次, 中村正治

    日本化学会春季年会講演予稿集(CD-ROM)   96th   ROMBUNNO.3J2‐09   2016.3

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  • 鉄触媒を用いたα-ハロエステルとアリールホウ素反応剤との不斉クロスカップリング反応

    奥園智絵美, 岩本貴寛, 岩本貴寛, ADAK Laksmikanta, 神将吉, 高谷光, 中村正治

    日本化学会春季年会講演予稿集(CD-ROM)   96th   2016

  • フッ化鉄/NHC触媒系を用いた芳香族塩化物とアルキルGrignard反応剤とのクロスカップリング反応と放射光X線吸収微細構造解析による反応機構解析

    縣亮介, 岩本貴寛, 岩本貴寛, 高谷光, 中村正治

    日本化学会春季年会講演予稿集(CD-ROM)   96th   2016

  • 鉄‐NHC触媒系を用いた芳香族塩化物のアルキル化反応の開発と放射光X線吸収分光による反応機構解析

    縣亮介, 岩本貴寛, 中川尚久, 磯崎勝弘, 畠山琢次, 高谷光, 中村正治

    有機合成シンポジウム講演要旨集   108th   108 - 109   2015.10

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  • 放射光の多角利用に基づく鉄錯体触媒の構造解析

    高谷光, 高谷光, 仲嶋翔, 仲嶋翔, 岩本貴寛, 岩本貴寛, 磯崎勝弘, 磯崎勝弘, 安田伸宏, 本間徹生, 高垣昌史, 砂田祐輔, 永島英夫, 中村正治, 中村正治

    日本結晶学会年会講演要旨集   2015   16   2015.10

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  • シクロパラフェニレンの励起三重項物性の環サイズ依存性

    藤塚守, LU Chao, 岩本貴寛, 茅原栄一, 山子茂, 真嶋哲朗

    光化学討論会講演要旨集   2015 ( CD-ROM )   ROMBUNNO.2P023   2015.9

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  • メタル化アミノ酸・ペプチドの合成と機能開拓

    高谷光, 高谷光, 吉田亮太, 吉田亮太, 伊藤蘭, 伊藤蘭, 横井友哉, 横井友哉, 岩本貴寛, 岩本貴寛, 岩本貴寛, 磯崎勝弘, 磯崎勝弘, 安田伸広, 中村正治, 中村正治

    高分子学会予稿集(CD-ROM)   64 ( 2 )   ROMBUNNO.2K05   2015.8

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  • Synthesis, Structure and Reactivity of Aryliron Intermediates in Iron-Catalyzed Cross-Coupling Reaction

    NAKAJIMA SHO, ISOZAKI KATSUHIRO, ISOZAKI KATSUHIRO, NAKAGAWA NAOHISA, NAKAGAWA NAOHISA, IMAYOSHI RYUJI, HASHIMOTO TORU, GOWER NICHOLAS J, ADAK LAKSMIKANTA, HONMA TETSUO, TAKAGAKI MASAFUMI, SUNADA YUSUKE, NAGASHIMA HIDEO, NAGASHIMA HIDEO, HASHIZUME DAISUKE, IWAMOTO TAKAHIRO, IWAMOTO TAKAHIRO, HATAKEYAMA TAKUJI, TAKAYA HIKARU, NAKAMURA MASAHARU

    Symp Organomet Chem Jpn   62nd   160   2015.8

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  • Properties of Triplet-Excited [n]Cycloparaphenylenes (n = 8–12)

    Fujitsuka, M, Lu,C, Iwamoto,T, Kayahara,E, Yamago,S, Majima,T

    The 11th Korea-Japan Symposium on Frontier Photoscience、Jeju,Korea   2015.6

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  • 鉄触媒によるアルキンのアンチ選択的カルボシリル化反応

    NISHIKORI TATSUSHI, NAKAGAWA NAOHISA, IWAMOTO TAKAHIRO, HATAKEYAMA TAKUJI, TAKAYA HIKARU, NAKAMURA MASAHARU

    日本化学会講演予稿集   95th ( 4 )   1308   2015.3

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  • ピンサー型ルテニウム錯体結合型ノルバリンペプチドの合成

    伊藤蘭, 吉田亮太, 横井友哉, 岩本貴寛, 磯崎勝弘, 高谷光, 中村正治

    日本化学会講演予稿集   95th ( 4 )   1297   2015.3

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  • シクロパラフェニレンラジカルイオン種の環サイズ依存性

    藤塚守, 藤乗幸子, 岩本貴寛, 茅原栄一, 山子茂, 真嶋哲朗

    日本化学会第95春季年会,船橋市   2015.3

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  • Structural Investigation of Cycloparaphenylene-Fullerene Supramolecular Complexes Using Synchrotron Radiation and Theoretical Calculation Reviewed

    岩本貴寛, 高谷光, 山子茂

    日本結晶学会誌   57 ( 4 )   239 - 244   2015

  • メタル化アミノ酸・ペプチド超分子の触媒作用

    高谷光, 磯崎勝弘, 吉田亮太, 横井友哉, 竹中健朗, 伊藤蘭, 岩本貴寛, 安田伸宏, 吉岡康一, 渡辺隆司, 中村正治

    高分子学会予稿集(CD-ROM)   63 ( 2 )   ROMBUNNO.1N07   2014.9

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  • New Organic Chemistry of Three-Dimensional pi-Conjugated Compounds Reviewed

    Shigeru Yamago, Eiichi Kayahara, Takahiro Iwamoto

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   72 ( 9 )   992 - 1005   2014.9

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    This article describes the most recent developments in the synthesis of three dimensional (3D) pi-conjugated molecules and the elucidation of their properties accomplished by the authors' group. Cycloparaphenylenes (CPPs) of different sizes and a cage-like 3D molecule were synthesized based on the platinum-mediated assembly of pi c-units and subsequent reductive elimination of platinum. The assembly of pi c-units mimics the self-assembly process for the formation of supra-molecular transition metal-ligand complexes with 3D cages and polyhedral structures. Furthermore, reductive elimination of platinum successfully took place with high efficiency, despite the high strain energy of the target molecule. Several size-dependent properties of CPPs, namely the photophysical, redox, and host-guest chemistries, were also clarified. These results are of use for a molecular-level understanding of CNT physical properties as well as fullerene peapods. Theoretical and electrochemical studies suggest that small CPPs and their derivatives should be excellent lead compounds for molecular electronics.

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  • 酸素官能基を持つシクロパラフェニレンの合成とその酸化還元挙動

    ONISHI HIROAKI, IWAMOTO TAKAHIRO, KAYAHARA EIICHI, YAMAGO SHIGERU

    基礎有機化学討論会要旨集   25th   152   2014.8

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  • Electron transfer in a supramolecular associate of a fullerene fragment

    Rafael M. Krick Calderon, Maria Gallego, Joaquin Calbo, Juan Arago, Fernando H. Liquido, Takahiro Iwamoto, Allison K. Greene, Edward A. Jackson, Emilio M. Perez, Enrique Orti, Dirk M. Guldi, Lawrence T. Scott, Nazario Martin

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   248   2014.8

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    Web of Science

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  • 酸素官能基を持つCPP類縁体の合成

    ONISHI HIROAKI, IWAMOTO TAKAHIRO, KAYAHARA EIICHI, YAMAGO SHIGERU

    日本化学会講演予稿集   94th ( 4 )   1160   2014.3

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  • シクロパラフェニレンとLa@C82との最短メタロフラーレンピーポッドの形成

    岩本貴寛, SLANINA Zdenek, GUO Jingdong, 溝呂木直美, 赤阪健, 加藤立久, 永瀬茂, 高谷光, 安田伸広, 山子茂

    日本化学会講演予稿集   94th ( 4 )   2014

  • 多角形有機金属錯体を前駆体とした環状共役π分子の新しい合成法の開発

    岩本 貴寛

    京都大学化学研究所スーパーコンピュータシステム研究成果報告書   2014   14 - 15   2014

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    平成25年度 京都大学化学研究所 スーパーコンピュータシステム 利用報告書

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  • かご型白金多核錯体を用いた含歪み三次元π共役系化合物の合成とその基礎的物性

    KAYAHARA EIICHI, IWAMOTO TAKAHIRO, TAKAYA HIKARU, SUZUKI TOSHIYASU, YAMAGO SHIGERU

    日本化学会講演予稿集   93rd ( 4 )   1088   2013.3

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  • 種々の炭素架橋鎖を持つシクロパラフェニレン誘導体の合成

    IWAMOTO TAKAHIRO, KOJIMA MITSURU, KAYAHARA EIICHI, YAMAGO SHIGERU

    日本化学会講演予稿集   93rd ( 4 )   1088   2013.3

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  • シクロパラフェニレンによるオニオン型超分子構造体の形成

    岩本貴寛, 倉知大介, 高谷光, 山子茂, 山子茂

    日本化学会講演予稿集   93rd ( 4 )   2013

  • 環状白金多核錯体を用いたシクロパラフェニレン類の新しい合成法の開発

    KAYAHARA EIICHI, IWAMOTO TAKAHIRO, KOJIMA MITSURU, YAMAGO SHIGERU

    有機合成シンポジウム講演要旨集   102nd   74 - 75   2012.10

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  • シクロパラフェニレン誘導体の合成とその物性

    KAYAHARA EIICHI, IWAMOTO TAKAHIRO, KOJIMA MITSURU, YAMAGO SHIGERU

    高分子学会予稿集(CD-ROM)   61 ( 2 )   ROMBUNNO.2F06   2012.9

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  • 白金四核錯体を前駆体としたシクロフェナントレンとその誘導体の合成

    IWAMOTO TAKAHIRO, KURACHI DAISUKE, KAYAHARA EIICHI, YAMAGO SHIGERU

    基礎有機化学討論会要旨集   23rd   12 - 13   2012.9

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  • シクロパラフェニレンとフラーレンとの超分子錯体の形成

    IWAMOTO TAKAHIRO, KAYAHARA EIICHI, TAKAYA HIKARU, HAINO TAKEHARU, YAMAGO SHIGERU

    高分子学会予稿集(CD-ROM)   61 ( 2 )   ROMBUNNO.1G09   2012.9

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  • シクロパラフェニレン前駆体である環状白金四核錯体の段階的合成

    TANAKA TAKESHI, KAYAHARA EIICHI, IWAMOTO TAKAHIRO, YAMAGO SHIGERU

    日本化学会講演予稿集   92nd ( 4 )   1493   2012.3

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  • ビスアリール白金マクロ環錯体を前駆体としたシクロパラフェニレンの合成 Reviewed

    渡邊由城, 岩本貴寛, 山子茂

    2009KIPS若手高分子シンポジウム ,京都   2009.12

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Presentations

  • Application of solution-phase XAFS for homogeneous catalyst: mechanistic study on iron-catalyzed cross-coupling reactions

    Takaya Hikaru, Nakajima Sho, Iwamoto Takahiro, Aoki Yuma, Agata Ryosuke, Suzuki Tsuyoshi, Isozaki Katsuhiro, Sunada Yusuke, Takagaki Masafumi, Honnma Tetsuo, Nagashima Hideo, Nakamura Masaharu

    Proceeding of Annual/Fall Meetings of the Japan Petroleum Institute  2016.11  公益社団法人 石油学会

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    放射光X線を用いるX線吸収分光(XAFS)の普及と量子科学計算をベースとしたXAFSシミュレーションに進歩によって、均一系分子触媒の溶液構造の精密構造解析を有機化学者が自らの手で手軽に行えるようになってきた。本講演では、常磁性のためNMR分析が困難な常磁性鉄錯体を用いる均一系触媒反応の機構研究において、溶液XAFSが極めて強力な手段となり、反応溶液中の触媒中間体の同定・構造決定に基づく精密な反応機構の決定が可能となることを紹介したい。

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  • 放射光X線吸収分光による鉄触媒の溶液構造解析

    高谷光, 仲嶋翔, 岩本貴寛, 岩本貴寛, 青木雄真, 縣亮介, 磯崎勝弘, 砂田祐輔, 高垣昌史, 本間徹生, 永島英夫, 永島英夫, 中村正治

    触媒討論会討論会A予稿集  2016.9 

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  • シクロパラフェニレンの酸化特性の解明

    橋本士雄磨, 岩本貴寛, 倉知大介, 河野太郎, 茅原栄一, 山子茂

    第25回基礎有機化学討論会  2016.9 

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  • 放射光で観る分子性錯体の溶液中分子構造と触媒作用

    高谷光, 仲嶋翔, 岩本貴寛, 岩本貴寛, 青木雄真, 縣亮介, 磯崎勝弘, 本間徹生, 高垣昌史, 為則雄祐, 永島英夫, 永島英夫, 砂田祐輔, 中村正治

    錯体化学会討論会講演要旨集  2016.8 

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  • フェニル鉄中間体の溶液構造解析に基づく鉄触媒クロスカップリング反応の機構研究

    仲嶋翔, 高谷光, 磯崎勝弘, 磯崎勝弘, 岩本貴寛, 岩本貴寛, 中川尚久, GOWER N.J, 今吉隆治, 本間徹生, 高垣昌史, 砂田祐輔, 永島英夫, 永島英夫, 畠山琢次, 中村正治

    日本化学会春季年会講演予稿集(CD-ROM)  2016.3 

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  • 鉄‐NHC触媒系を用いた芳香族塩化物のアルキル化反応の開発と放射光X線吸収分光による反応機構解析

    縣亮介, 岩本貴寛, 中川尚久, 磯崎勝弘, 畠山琢次, 高谷光, 中村正治

    有機合成シンポジウム講演要旨集  2015.10 

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  • 放射光の多角利用に基づく鉄錯体触媒の構造解析

    高谷光, 高谷光, 仲嶋翔, 仲嶋翔, 岩本貴寛, 岩本貴寛, 磯崎勝弘, 磯崎勝弘, 安田伸宏, 本間徹生, 高垣昌史, 砂田祐輔, 永島英夫, 中村正治, 中村正治

    日本結晶学会年会講演要旨集  2015.10 

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  • メタル化アミノ酸・ペプチドの合成と機能開拓

    高谷光, 高谷光, 吉田亮太, 吉田亮太, 伊藤蘭, 伊藤蘭, 横井友哉, 横井友哉, 岩本貴寛, 岩本貴寛, 岩本貴寛, 磯崎勝弘, 磯崎勝弘, 安田伸広, 中村正治, 中村正治

    高分子学会予稿集(CD-ROM)  2015.8 

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  • Synthesis, Structure and Reactivity of Aryliron Intermediates in Iron-Catalyzed Cross-Coupling Reaction

    NAKAJIMA SHO, ISOZAKI KATSUHIRO, ISOZAKI KATSUHIRO, NAKAGAWA NAOHISA, NAKAGAWA NAOHISA, IMAYOSHI RYUJI, HASHIMOTO TORU, GOWER NICHOLAS J, ADAK LAKSMIKANTA, HONMA TETSUO, TAKAGAKI MASAFUMI, SUNADA YUSUKE, NAGASHIMA HIDEO, NAGASHIMA HIDEO, HASHIZUME DAISUKE, IWAMOTO TAKAHIRO, IWAMOTO TAKAHIRO, HATAKEYAMA TAKUJI, TAKAYA HIKARU, NAKAMURA MASAHARU

    Symp Organomet Chem Jpn  2015.8 

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  • Properties of Triplet-Excited [n]Cycloparaphenylenes (n = 8–12)

    Fujitsuka, M, Lu,C, Iwamoto,T, Kayahara,E, Yamago,S, Majima,T

    The 11th Korea-Japan Symposium on Frontier Photoscience、Jeju,Korea  2015.6 

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  • 鉄触媒によるアルキンのアンチ選択的カルボシリル化反応

    NISHIKORI TATSUSHI, NAKAGAWA NAOHISA, IWAMOTO TAKAHIRO, HATAKEYAMA TAKUJI, TAKAYA HIKARU, NAKAMURA MASAHARU

    日本化学会講演予稿集  2015.3 

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  • ピンサー型ルテニウム錯体結合型ノルバリンペプチドの合成

    伊藤蘭, 吉田亮太, 横井友哉, 岩本貴寛, 磯崎勝弘, 高谷光, 中村正治

    日本化学会講演予稿集  2015.3 

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  • シクロパラフェニレンラジカルイオン種の環サイズ依存性

    藤塚守, 藤乗幸子, 岩本貴寛, 茅原栄一, 山子茂, 真嶋哲朗

    日本化学会第95春季年会,船橋市  2015.3 

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  • メタル化アミノ酸・ペプチド超分子の触媒作用

    高谷光, 磯崎勝弘, 吉田亮太, 横井友哉, 竹中健朗, 伊藤蘭, 岩本貴寛, 安田伸宏, 吉岡康一, 渡辺隆司, 中村正治

    高分子学会予稿集(CD-ROM)  2014.9 

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  • ビスアリール白金マクロ環錯体を前駆体としたシクロパラフェニレンの合成

    渡邊由城, 岩本貴寛, 山子茂

    2009KIPS若手高分子シンポジウム ,京都  2009.12 

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Awards

  • 日本化学会BCSJ賞

    2019  

    岩本 貴寛

  • 有機合成化学協会研究企画賞

    2016  

    岩本 貴寛

  • 日本化学会BCSJ賞

    2015  

    岩本 貴寛

  • 公益財団法人MSD生命科学財団 第3回大津会議フェロー

    2012  

    岩本 貴寛

Research Projects

  • Development of beta-carbon elimination reactions of alkynes from unstrained vinyl complexes

    Grant number:21K05101  2021.4 - 2024.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)  Chuo University

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    Grant amount: \4160000 ( Direct Cost: \3200000 、 Indirect Cost: \960000 )

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  • 3d遷移金属触媒用のNキラル配位子の創製

    Grant number:20K05493  2020.4 - 2023.3

    日本学術振興会  科学研究費助成事業  基盤研究(C)  中央大学

    岩本 貴寛

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    Grant amount: \4290000 ( Direct Cost: \3300000 、 Indirect Cost: \990000 )

    前年度までに、目的配位子のグラムスケールでの合成法確立とパラジウムを使ったモデル錯体合成に成功している。また、モデル錯体の検討において、錯形成時にリン上キラリティーから窒素上へのキラリティー転写が効率的に起こり、特定の窒素上置換基では立体選択的に錯体が得られることを見出した。
    これらの検討結果から配位子設計概念の妥当性を実証できたことから、今年度は本研究の目的である3d遷移金属錯体の合成を検討した。中でも、金属として鉄の利用に焦点を当てた。多種多様な中性鉄前駆体との錯形成を検討したが、鉄錯体の合成には至らなかった。一般に、鉄とリンなどの補助配位子との配位はパラジウムなどと比べ弱く、系中での配位子解離が問題となることがあるが、本配位子系においても配位子と鉄との配位力が弱いために平衡が配位子解離に偏っていることが明らかとなった。種々の検討を行った結果、カチオン性鉄前駆体を利用することで鉄錯体の合成が可能であることが分かった。鉄錯体が常磁性であり、窒素上キラリティーを含む錯体構造の完全な決定には至っていないため、今後単結晶X線構造解析による錯体の同定を進めていく。
    上述の通り、本配位子と鉄との配位力の弱さは触媒反応への応用の際に触媒失活などの問題となることが予想される。そこで、配位力の向上を目指し、キラルリン配位子に対して新たな配位部位の導入を行っている。本検討を通して、堅牢な鉄錯体の創製を目指す。

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  • Development of Halogenation Reaction with Salt by Photocatalyst

    Grant number:18K14215  2018.4 - 2020.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Early-Career Scientists  Kyoto University

    Iwamoto Takahiro

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    Grant amount: \4160000 ( Direct Cost: \3200000 、 Indirect Cost: \960000 )

    Organic halides represent important classes of chemicals in organic chemistry. Although halogenation reactions have been established firmly in chemical industry, these processes require huge amount of energy. As an ideal halogenation reaction, we here examined halogenation reactions by using halide salts. As a result, we have developed a novel photocatalyst having phase-transfer ability, and succeeded its application to catalytic bromination with potassium bromide. The present results indicated that such phase-transfer photocatalysts would have great potential as a catalyst of halogenation reactions with halide salts.

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  • Development of Aromatic C-H Functionalization Triggered by Cation-pi Interaction

    Grant number:15K17854  2015.4 - 2017.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Young Scientists (B)  Kyoto University

    Iwamoto Takahiro

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    Selective C-H functionalization of simple arenes with no directing group still remains challenges. Catalytic system utilizing substrate-ligand interaction is a powerful approach to exhibit excellent reactivity and selectivity. In the previous reports, substrate-ligand interactions are limited to hydrogen bond, pi-stacking or acid-base interaction. Therefore substrates require some functional groups. For C-H functionalization of simple arene, I herein examined cation-pi interaction between arene substrate and ligand.
    I succeeded in preparing a variety of ligands having diverse linkers. Catalytic activity of these ligands was next examined in several C-H functionalization of benzene, while reactions hardly proceeded in all cases. NMR study indicated that activation ability of the ligands was little for accelerating the C-H activation process. However, during these reaction screening, novel C-H functionalization of amine was discovered.

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  • カチオン-π相互作用を鍵とした芳香族C-H活性化反応の開発

    Grant number:26888009  2014.8 - 2015.3

    日本学術振興会  科学研究費助成事業  研究活動スタート支援  京都大学

    岩本 貴寛

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    Grant amount: \1300000 ( Direct Cost: \1000000 、 Indirect Cost: \300000 )

    本研究では、カチオン-π相互作用を鍵とした芳香族C-H官能基化反応の開発を目指し検討を行った。従来のC-H官能基化反応の多くは、配位性官能基と遷移金属触媒との相互作用を鍵としている為に、基質は配位性官能基を持つものに限られる、かつ配位性官能基から空間的に離れた位置でのC-H官能基化は困難であるといった欠点があった。本研究ではこれらの問題を克服するために、1)配位性官能基を必要としない反応、2)カチオン-π相互作用による基質の活性化と認識を利用した高選択的な反応の二点に焦点を当てた触媒設計を行った。触媒設計の鍵は金属カチオンを取り込むためのアザクラウンユニットを持つ点であり、まず理論計算によりアザクラウンユニットと遷移金属に対する配位子となるユニットを繋ぐリンカー部分の最適化を行った。得られた知見に基づいて、アザクラウンユニットを持つ配位子の合成を行ったところ、様々な長さのアルキル基をリンカーとする配位子の合成に成功した。また、柔軟なアルキル基に加えて、剛直な芳香環をリンカーとする配位子を合成することにも成功した。特に、開発した合成法はアザクラウンを原料として短工程での合成が可能であると共に、グラムスケールでの合成も可能であったことから、今後多彩な配位子の設計、合成を行う上で有用なものになると考えている。今後は、実際のC-H官能基化反応を行い、本触媒系の有用性を実証すると共に、得られた知見を触媒設計にフィードバックすることで高効率、高選択的でかつシンプルな触媒の開発を行う。

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  • 多角形有機金属錯体を前駆体とした環状共役π分子の新しい合成法の開発

    Grant number:11J03609  2011 - 2014.3

    日本学術振興会  科学研究費助成事業  特別研究員奨励費  京都大学

    岩本 貴寛

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    Grant amount: \1900000 ( Direct Cost: \1900000 )

    シクロパラフェニレン(CPP)は、ベンゼン環がパラ位で結合した環状構造を有しており、その構造はアームチェア型カーボンナノチューブ(CNT)の最小構成単位である。よって、CNTと同様に空孔を利用したホストゲスト錯体の形成が期待できる。すでに、昨年度までに[10] CPPがC60をサイズ選択的に包摂し、最短のC60ピーポッドを形成することを明らかにしている。また、すでにC70をゲスト分子として用いた際も、[10]および[11] CPPがそれぞれC70を包摂することを明らかにしていたが、錯体の構造は理論計算により推定したのみであった。今年度は、C70とCPP、との錯体のX線結晶構造解析による構造の決定を行うと共に、これまでの空のフラーレンとは異なり、特異な電子状態を持つLa@C82との錯形成を検討した。その結果、単結晶X線構造解析の結果から、[10] CPP内ではC70の短径方向でCPPと相互作用した"Lying"と呼ばれる配向を取っていた。一方で、[11] CPP内では、C70の長径方向でCPPと相互作用した"Standing"と呼ばれる配向を取ることを実験的に明らかにした。La@C82との錯形成では、これまでと同様に特定の環サイズを持つCPPとのサイズ選択的な錯形成を明らかにし、X線結晶構造解析により錯体の構造を決定することに成功した。加えて、電気化学測定とともに理論計算を行うことで、CPPからLa@C82への部分電荷移動を観測することに成功した。これはピーポッドにおける電子的な相互作用を明らかにした初めての例である。以上の結果は、CPPをホスト分子とした新規超分子構造体の創成に繋がる結果であると共に、CNTピーポッドにおけるCNTとフラーレン間の相互作用を分子レベルで明らかにしたものであり、曲面上π分子間に働く相互作用を理解するうえで重要な知見を与えるものと考えている。

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