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論文 - 福井　識人

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Acridino[2,1,9,8-klmna]acridine Bisimides: An Electron-Deficient pi-System for Robust Radical Anions and n-Type Organic Semiconductors 査読有り

Keita Tajima, Kyohei Matsuo, Hiroko Yamada, Shu Seki, Norihito Fukui, Hiroshi Shinokubo

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 60 巻 ( 25 ) 頁： 14060 - 14067 2021年6月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：WILEY-V C H VERLAG GMBH

We report the synthesis and properties of acridino[2,1,9,8-klmna]acridine bisimide (AABI), a nitrogen-doped anthanthrene with two imide functionalities. AABI exhibits excellent electron affinity as evident by its low-lying LUMO level (-4.1 eV vs. vacuum). Single-electron reduction of one AABI derivative afforded the corresponding radical anion, which was stable under ambient conditions. Photoconductivity measurements suggest that the intrinsic electron mobility of an N-phenethyl AABI derivative obeys a band-transport model. Accordingly, an electron mobility of 0.90 cm(2) V-1 s(-1) was attained with the corresponding single-crystal organic field-effect transistor (OFET) device. The vacuum-deposited OFET device consisting of a polycrystalline sample exhibited high electron mobility of up to 0.27 cm(2) V-1 s(-1) even in air. This study demonstrates that dual incorporation of both imide substituents and imine-type nitrogen atoms is an effective strategy to create novel electron-deficient pi-systems.

DOI： 10.1002/anie.202102708

Web of Science

Non-Planar Perylene Bisimide Analogues with Inserted Carbonyl and Methylene Subunits 査読有り

Mai Odajima, Keita Tajima, Norihito Fukui, Hiroshi Shinokubo

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 2021年6月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：WILEY-V C H VERLAG GMBH

The synthesis and properties of dinaphthotropone bisimide (DNTrBI) and dinaphthocycloheptatriene bisimide (DNCHepBI) are described. Their molecular design is conceptually based on the insertion of a carbon atom into a perylene bisimide (PBI) core. These molecules adopt non-planar structures due to the presence of a seven-membered ring. The PBI derivative into which a carbonyl group was inserted (DNTrBI) immediately underwent nonradiative decay and/or intersystem crossing in its excited state. The PBI derivative into which a methylene group was inserted (DNCHepBI) was susceptible to deprotonation on account of the two electron-withdrawing naphthalene monoimide units. Subsequent aerobic oxidation resulted in the formation of a C-C bond at the central methylene unit, thus affording a sigma-dimer. The formation of this C-C bond is dynamically redox-active, i.e., electron injection into the sigma-dimer almost quantitatively regenerated the deprotonated DNCHepBI.

DOI： 10.1002/anie.202104882

Web of Science

Dinaphtho[1,8-bc:1 ',8 '-fg][1,5]dithiocine Bisimide 査読有り

Yuki Tanaka, Keita Tajima, Norihito Fukui, Hiroshi Shinokubo

ASIAN JOURNAL OF ORGANIC CHEMISTRY 10 巻 ( 3 ) 頁： 541 - 544 2021年3月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：WILEY-V C H VERLAG GMBH

V-shaped pi-systems are attractive research targets in organic chemistry and materials science. Our group has recently demonstrated that the conceptual insertion of a heteroatom into a perylene bisimide (PBI) core is an effective guideline for the design of non-planar PBI derivatives. Here we report the synthesis and properties of dinaphtho[1,8-bc:1 ',8 '-fg][1,5]dithiocine bisimide (DNDTBI), which represents a doubly sulfur-inserted PBI derivative. The X-ray diffraction analysis revealed that DNDTBI adopted a V-shaped structure with a dihedral angle of 67 degrees. DNDTBI exhibited higher electron-donating ability than singly sulfur-inserted PBI derivative owing to the antibonding interaction between the two neighboring sulfur atoms. The inversion barrier of the flipping motion of DNDTBI was ca. 30 kcal mol(-1), indicating the rigid nature of the V-shaped structure.

DOI： 10.1002/ajoc.202000722

Web of Science

as-Indaceno[3,2,1,8,7,6-ghijklm]terrylene as a near-infrared absorbing C-70-fragment 査読有り

Yuki Tanaka, Norihito Fukui, Hiroshi Shinokubo

NATURE COMMUNICATIONS 11 巻 ( 1 ) 2020年8月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：NATURE PUBLISHING GROUP

Carbon and hydrogen are fundamental components of organic molecules and a fascinating plethora of functions can be generated using these two elements. Yet, realizing attractive electronic structures only by using carbon and hydrogen remains challenging. Herein, we report the synthesis and properties of the C-70 fragment as-indaceno[3,2,1,8,7,6-ghijklm]terrylene, which exhibits near-infrared (NIR) absorption (up to ca. 1300nm), even though this molecule consists of only 34 carbon and 14 hydrogen atoms. A remarkably small highest occupied molecular orbital-lowest unoccupied molecular orbital (HOMO-LUMO) gap is confirmed by electrochemical measurement and theoretical calculations. Furthermore, as-indacenoterrylene is stable despite the absence of peripheral substituents, which contrasts with the cases of other NIR-absorbing hydrocarbons such as diradicaloids and antiaromatic molecules. The results of this study thus offer fundamental insights into the design of hydrocarbons with a small band gap. The synthesis of hydrocarbons with attractive electronic structures remains challenging. Here, the authors describe the synthesis and properties of the C70 fragment as-indaceno[3,2,1,8,7,6-ghijklm]terrylene, which exhibits near-infrared (NIR) absorption.

DOI： 10.1038/s41467-020-17684-6

Web of Science

その他リンク： http://www.nature.com/articles/s41467-020-17684-6

Dinaphthothiepine Bisimide and Its Sulfoxide: Soluble Precursors for Perylene Bisimide 査読有り

Hayakawa, S., Matsuo, K., Yamada, H., Fukui, N., Shinokubo, H.

Journal of the American Chemical Society 142 巻 ( 27 ) 頁： 11663 - 11668 2020年7月

Inserting Nitrogen: An Effective Concept To Create Nonplanar and Stimuli-Responsive Perylene Bisimide Analogues 査読有り

Sakiho Hayakawa, Ayumi Kawasaki, Yongseok Hong, Daisuke Uraguchi, Takashi Ooi, Dongho Kim, Tomoyuki Akutagawa, Norihito Fukui, Hiroshi Shinokubo

Journal of the American Chemical Society 2019年12月

Aggregation-Induced Emission of Nitrogen-Bridged Naphthalene Monoimide Dimers 査読有り

Keita Tajima, Norihito Fukui, Hiroshi Shinokubo

ORGANIC LETTERS 21 巻 ( 23 ) 頁： 9516 - 9520 2019年12月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：AMER CHEMICAL SOC

We have prepared four 4-aminonaphthalene monoimide derivatives and examined the aggregation-induced emission (AIE) properties. A nitrogen-bridged dimer is AIE-active and exhibits bright green emission with a high quantum yield in the solid state. The X-ray diffraction analysis suggests that key to the bright luminescence is the favorable crystal packing dominated by CH/p interaction. The late-stage cyanation of the dimer tuned its AIE color from green to orange.

DOI： 10.1021/acs.orglett.9b03699

Web of Science

Singly and Doubly Sulfone-Inserted Porphyrin Arch-Tape Dimers 査読有り

Fukui Norihito, Osuka Atsuhiro

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 91 巻 ( 7 ) 頁： 1131 - 1137 2018年7月

Singly and Doubly 1,2-Phenylene-Inserted Porphyrin Arch-Tape Dimers: Synthesis and Highly Contorted Structures 査読有り

Norihito Fukui, Atsuhiro Osuka

Angewandte Chemie - International Edition 57 巻 ( 21 ) 頁： 6304 - 6308 2018年5月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Wiley-VCH Verlag

Singly and doubly 1,2-phenylene-inserted NiII porphyrin arch-tape dimers 3 and 9 were synthesized from the corresponding β-to-β 1,2-phenylene-bridged NiII porphyrin dimers 5 and 11 via Ni0-mediated reductive cyclization and DDQ/Sc(OTf)3-promoted oxidative cyclization as key steps, respectively. Owing to the fused eight-membered ring(s), 3 showed a more contorted structure than those of previously reported arch-tape dimers 2 a and 2 b possessing a fused seven-membered ring. Furthermore, 9 displayed much larger molecular contortion. As the molecular contortion increases, the Q band of the absorption spectrum becomes more red-shifted and the electrochemcial HOMO–LUMO gap becomes smaller, reaching at 1294 nm and 0.77 eV in 9, respectively. The effect of molecular contortion on the electronic properties was studied by means of DFT calculations.

DOI： 10.1002/anie.201802494

Web of Science

Scopus

Embedding heteroatoms: an effective approach to create porphyrin-based functional materials 査読有り

Norihito Fukui, Keisuke Fujimoto, Hideki Yorimitsu, Atsuhiro Osuka

DALTON TRANSACTIONS 46 巻 ( 39 ) 頁： 13322 - 13341 2017年10月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：ROYAL SOC CHEMISTRY

Incorporation of planarized heteroatom(s) onto the porphyrin periphery is an effective approach to create porphyrin-based functional materials. In the last three decades, such an "embedding heteroatom" strategy has been actively explored in order to realize attractive electronic, optical, and electrochemical properties. This review aims to cover a variety of synthetic methodologies that have been developed for the construction of heteroatom-embedded porphyrins. Moreover, we also summarize their structure-property relationships as well as possible applications in various research fields including artificial photosynthesis, molecular engineering, organic electronics, and bioimaging.

DOI： 10.1039/c7dt02815f

Web of Science

Porphyrin Arch-Tapes: Synthesis, Contorted Structures, and Full Conjugation 査読有り

Norihito Fukui, Taeyeon Kim, Dongho Kim, Atsuhiro Osuka

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 139 巻 ( 26 ) 頁： 9075 - 9088 2017年7月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：AMER CHEMICAL SOC

Porphyrin tapes possessing meso-meso beta-beta beta-beta triple direct linkages have been targets of extensive studies because of their fully conjugated characteristic pi-electronic networks. In this paper, we report porphyrin arch tapes that bear additional carbonyl group(s) or methylene group(s) inserted between one of the beta-beta linkage(s) of the porphyrin tapes. The carbonyl-inserted porphyrin arch-tapes were efficiently synthesized by double fusion reactions of beta-to-beta carbonyl-bridged porphyrin oligomers with DDQ and Sc(OTf)(3), and were converted to the methylene-bridged porphyrin arch-tapes via Luche reduction with NaBH4 and CeCl3 followed by ionic hydrogenation with HBF4 center dot OEt2 and BH3 center dot NEt3. While the conventional porphyrin tapes display rigid and planar structures and low solubilities, these porphyrin arch-tapes show remarkably contorted structures, flexible conformations, and improved solubilities because of the presence of the incorporated seven-membered ring(s). Interestingly, the methylene inserted arch-tapes exhibited conjugative electronic interactions that were comparable to those of porphyrin tapes probably owing to through-space interaction in the contorted conformations. The carbonyl-inserted arch-tapes displayed distinctly larger conjugative interactions owing to an active involvement of the carbonyl group(s) in the electronic conjugation. A similar trend was observed in the nonlinear optical properties, as evidenced by their two-photon absorption cross sections. Furthermore, as a benefit of the contorted structures, these porphyrin arch-tapes can catch C-60 fullerene effectively. Naturally, the electron-rich methylene-bridged arch-tapes exhibited larger association constants than the electron-deficient carbonyl-bridged arch-tapes. Among these arch-tapes, a methylene-bridged syn-Ni(II) porphyrin trimer recorded the largest association constant of (1.5 +/- 0.4) X 10(7) M-1 in toluene at 25 degrees C.

DOI： 10.1021/jacs.7b05332

Web of Science

meso-to-meso Pt-II-bridged Ni-II-porphyrin dimers 査読有り

Norihito Fukui, Hua-Wei Jiang, Atsuhiro Osuka

ORGANIC CHEMISTRY FRONTIERS 4 巻 ( 5 ) 頁： 767 - 772 2017年5月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：ROYAL SOC CHEMISTRY

The synthesis and characterization of meso-to-meso Pt-II-bridged Ni-II-porphyrin dimers 5-7 are reported herein. A boron-platinum exchange reaction of meso-pinacolatoborylporphyrin 8 with Pt(cod) Cl-2 afforded the cod-coordinated meso-to-meso Pt-II-linked cis-dimer 5, which was subsequently converted to the 1,3-bis(diphenylphosphino) propane (DPPP)-coordinated cis-dimer 6 and the PPh3-coordinated trans-dimer 7 upon treatment with DPPP and PPh3, respectively. On the other hand, a reaction of 5 with tri-tert-butylphosphine induced reductive elimination to give the meso-meso directly linked diporphyrin 9. Comparative studies of these Pt-II-bridged Ni-II-porphyrin dimers were conducted by UV/Vis absorption spectroscopy, electrochemical studies, and theoretical calculations. In the course of these studies, we found that cis-dimers 5 and 6 underwent an unprecedented reductive elimination to give the mesomeso linked dimer 9 upon chemical or electrochemical one-electron oxidation, while trans-dimer 7 was stable under such conditions.

DOI： 10.1039/c7qo00093f

Web of Science

Highly planar diarylamine-fused porphyrins and their remarkably stable radical cations 査読有り

Norihito Fukui, Wonhee Cha, Daiki Shimizu, Juwon Oh, Ko Furukawa, Hideki Yorimitsu, Dongho Kim, Atsuhiro Osuka

CHEMICAL SCIENCE 8 巻 ( 1 ) 頁： 189 - 199 2017年1月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：ROYAL SOC CHEMISTRY

Oxidative fusion reactions of meso-phenoxazino Ni(II) porphyrin were found to be temperature dependent, giving rise to either a doubly phenylene-fused product at room temperature or a singly phenoxazine-fused product at 70 degrees C. The latter was further oxidized to a doubly phenoxazine-fused Ni(II) porphyrin, which was subsequently converted to the corresponding free base porphyrin and Zn(II) porphyrin. Compared to previously reported diphenylamine-fused porphyrins that displayed a molecular twist, doubly phenoxazine-fused porphyrins exhibited distinctly different properties owing to their highly planar structures, such as larger fluorescence quantum yields, formation of an offset face-to-face dimer both in solution and the solid state, and the generation of a mixed-valence p-radical cation dimer upon electrochemical oxidation. One-electron oxidation of the phenoxazine-fused Ni(II) porphyrin with Magic Blue gave the corresponding radical cation, which was certainly stable and could be isolated by separation over a silica gel column but slowly chlorinated at the reactive beta-positions in the solid state. This finding led to us to examine beta, beta'-dichlorinated phenoxazine-fused and diphenylamine-fused Ni(II) porphyrins, which, upon treatment with Magic Blue, provided remarkably stable radical cations to an unprecedented level. It is actually possible to purify these radical cations by silica gel chromatography, and they can be stored for over 6 months without any sign of deterioration. Moreover, they exhibited no degradation even after the CH2Cl2 solution was washed with water. However, subtle structural differences (planar versus partly twisted) led to different crystal packing structures and solid-state magnetic properties.

DOI： 10.1039/c6sc02721k

Web of Science

Homochiral and Heterochiral Self‐Sorting Assemblies of Antiaromatic Ni(II) Norcorrole Dimers 査読有り

Si‐Yu Liu, Sha Li, Shusaku Ukai, Ryo Nozawa, Norihito Fukui, Ryota Sugimori, Ryohei Kishi, Hiroshi Shinokubo

Chemistry – A European Journal 30 巻 ( 39 ) 2024年5月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Wiley

Abstract

Recently, π–π stacked antiaromatic π‐systems have received considerable attention because they can exhibit stacked‐ring aromaticity due to substantial intermolecular orbital interactions. Here, we report three antiaromatic norcorrole dimers that self‐assemble to form supramolecular architectures through chiral self‐sorting. A 2,2’‐linked norcorrole dimer with 3,5‐di‐tert‐butylphenyl groups forms a π‐stacked dimer both in solid and solution states via homochiral self‐sorting. Its association constant in solution is (3.6±1.7)×10<sup>5</sup> M<sup>−1</sup> at 20 °C. In the solid state, 3,3’‐linked norcorrole dimers with 3,5‐di‐tert‐butylphenyl and phenyl groups afford macrocyclic and helical supramolecular assemblies via heterochiral and homochiral self‐sorting, respectively. Notably, the subtle modification in the substituent resulted in a complete change in the structure of the aggregates and the chiral self‐sorting mode. The present findings demonstrate that structural manipulation in antiaromatic monomer units leads to the formation of various supramolecular assemblies on the basis of the attractive interactions between antiaromatic π‐systems.

DOI： 10.1002/chem.202400292

Changing aromatic properties through stacking: the face-to-face dimer of Ni(<scp>ii</scp>) bis(pentafluorophenyl)norcorrole 査読有り

Qian Wang, Dage Sundholm, Jürgen Gauss, Tommaso Nottoli, Filippo Lipparini, Shota Kino, Shusaku Ukai, Norihito Fukui, Hiroshi Shinokubo

Physical Chemistry Chemical Physics 26 巻 ( 20 ) 頁： 14777 - 14786 2024年5月

Close Stacking of Antiaromatic Ni(II) Norcorrole Originating from a Four-Electron Multicentered Bonding Interaction 査読有り

Shota Kino, Shusaku Ukai, Norihito Fukui, Rie Haruki, Reiji Kumai, Qian Wang, Satoshi Horike, Quan Manh Phung, Dage Sundholm, Hiroshi Shinokubo

Journal of the American Chemical Society 146 巻 ( 13 ) 頁： 9311 - 9317 2024年3月

A Triply Linked Porphyrin‐Norcorrole Hybrid with Singlet Diradical Character 査読有り

Kaisheng Wang, Satoru Ito, Shuang Ren, Daiki Shimizu, Norihito Fukui, Ryohei Kishi, Qiang Liu, Atsuhiro Osuka, Jianxin Song, Hiroshi Shinokubo

Angewandte Chemie International Edition 2024年2月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Wiley

Abstract

Norcorrole Ni(II) complexes have recently received considerable attention because they are readily accessible antiaromatic molecules. Their high stability under ambient conditions and ease of synthesis have enabled the exploration of the intrinsic properties of antiaromatic molecules. Here, we report the synthesis and properties of meso–meso singly linked porphyrin‐norcorrole hybrids and a triply linked porphyrin‐norcorrole hybrid. The singly linked and triply linked porphyrin‐norcorrole hybrids were fully characterized, including an X‐ray structural analysis. Due to their orthogonal conformation, the singly linked hybrids maintain the individual electronic properties of their porphyrin and norcorrole subunits, while the triply linked hybrid shows a significantly smaller electrochemical HOMO–LUMO gap (0.45 eV) than that of Ni(II) dimesitylnorcorrole (1.08 eV). Furthermore, the triply linked hybrid exhibits singlet diradical characteristics, as confirmed by VT NMR, ESR, and SQUID experiments.

DOI： 10.1002/anie.202401233

Supramolecular Assemblies of Closely Stacked Antiaromatic Ni(II) Norcorrole Dimers via Homochiral and Heterochiral Self-Sorting 査読有り

Si-Yu Liu, Shusaku Ukai, Ryo Nozawa, Norihito Fukui, Ryota Sugimori, Ryohei Kishi, Hiroshi Shinokubo

2023年11月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：American Chemical Society (ACS)

Stacking between aromatic π-systems is fundamental to the design of supramolecular assemblies. Recently, π–π stacked antiaromatic π-systems have received considerable attention as some antiaromatic compounds can form closely stacked structures with substantial in-termolecular orbital interactions, resulting in the emergence of stacked-ring aromaticity. Here, we report three covalently linked norcor-role dimers that self-assemble to form supramolecular architectures. A 2,2’-linked norcorrole dimer with 3,5-di-tert-butylphenyl groups forms a face-to-face stacked dimer both in solid and solution states via homochiral self-sorting. Its association constant in solution is (3.6 ± 1.7) × 105 M–1 at 20 °C. In the solid state, 3,3’-linked norcorrole dimers with 3,5-di-tert-butylphenyl and phenyl groups afford macro-cyclic and helical supramolecular assemblies via heterochiral and homochiral self-sorting, respectively. Notably, the subtle modification in the substituent resulted in a complete change in the structure of the aggregates and the chiral self-sorting mode. The present findings demonstrate that structural manipulation in antiaromatic monomer units leads to the formation of various supramolecular assemblies on the basis of the attractive interactions between antiaromatic π-systems.

DOI： 10.26434/chemrxiv-2023-87qjz

A Double Bond Between Two Molecules 査読有り

Shota Kino, Shusaku Ukai, Norihito Fukui, Rie Haruki, Reiji Kumai, Qian Wang, Satoshi Horike, Quan Manh Phung, Dage Sundholm, Hiroshi Shinokubo

2023年11月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：American Chemical Society (ACS)

π-Conjugated molecules with one electronic spin often form π-stacked dimers via molecular-orbital interactions between the two unpaired electrons. These interactions are recognized as intermolecular single bonds between two π-conjugated systems. This then raises the question if a double bond between two such molecules is possible. To answer this question, we have synthesized an antiaromatic Ni(II) bis(pentafluorophenyl)norcorrole. Its dimer adopts a face-to-face-stacked structure with an extremely short stacking distance of 2.97 Å. Importantly, an intermolecular double bond does indeed exist in this system and this bond involves four bonding electrons between the two molecules. The bonding electrons were experimentally observed via synchrotron X-ray diffraction analysis and corroborated by theoretical calculations. The intermolecular interaction of the molecular orbitals imparts the stacked dimer with an aromatic character that is distinctly different from that of its monomer.

DOI： 10.26434/chemrxiv-2023-2brcz

Inner-Bond Cleavage in Nanographenes: A Constructive Destruction Strategy for Facile Access to Molecules with Multiple Figure-Eight Structures 査読有り

Yuki Sakamoto, Junichiro Hirano, Emiko Nishimoto, Daisuke Owase, Ren Takayanagi, Keita Tajima, Takuya Omine, Fumitaka Ishiwari, Akinori Saeki, Jinseok Kim, Juwon Oh, Dongho Kim, Tomoyuki Ikai, Eiji Yashima, Hiroshi Shinokubo, Norihito Fukui

2023年5月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：American Chemical Society (ACS)

The elegant architectures of nonplanar π-systems, such as fullerene and corannulene, exhibit distinctive functionalities that have played a significant role in advancing science and technology. The current approach to synthesizing nonplanar π-systems heavily relies on the stepwise formation of bonds between their constituent fragments, which is known as the bottom-up approach. The limited number of synthetic pathways to nonplanar π-systems inevitably results in impractical molecular frameworks. Herein, we demonstrate that a constructive destruction approach, based on the oxidative cleavage of internal double bonds of dibenzo[g,p]chrysene that immediately produces eightphenone: the first readily available figure-eight molecule. Eightphenone adopts a D2-symmetric structure with excellent configurational stability and is a highly efficient emitter of circularly polarized phosphorescence. The oxidative cleavage of internal double bonds is also applicable to larger nanographene molecules, resulting in unprecedented structures with multiple figure-eight units. This study introduces the concept of constructive destruction as an alternative to conventional bottom-up approaches, paving the way for the design of new materials.

DOI： 10.26434/chemrxiv-2023-f1djk-v2

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