Faculty Profiles - SHINOKUBO, Hiroshi

Papers - SHINOKUBO, Hiroshi

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Stepwise N-Methylation of Ruthenium and Cobalt 5,15-Diazaporphyrins: Post-Functionalization of Porphyrinoid Catalysts Reviewed International journal

Nishijo Mayu, Mori Shiho, Nishimura Tsubasa, Shinokubo Hiroshi, Miyake Yoshihiro

CHEMISTRY-AN ASIAN JOURNAL Vol. 17 ( 14 ) page： e202200305 2022.7

Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Chemistry - An Asian Journal

Post-functionalization of porphyrinoid catalysts provides a powerful tool for fine-tuning their electronic structure. We have succeeded in the stepwise methylation of the peripheral nitrogen atoms in ruthenium and cobalt 5,15-diazaporphyrins. The axial coordination of an anion to the metal center accelerates the second methylation through charge neutralization. N-Methylation of the diazaporphyrin complexes effectively controls their electron deficiency, Lewis acidity, and catalytic activity.

DOI： 10.1002/asia.202200305

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Protonation‐Induced Antiaromaticity in Octaaza[8]circulenes: Cyclooctatetraene Scaffolds Constrained with Four Amidine Moieties Reviewed International coauthorship International journal

Shuhei Akahori, Atsushi Kaga, Jinseok Kim, Hideki Yorimitsu, Dongho Kim, Hiroshi Shinokubo, Yoshihiro Miyake

Chemistry – An Asian Journal Vol. 17 ( 12 ) page： e202200244 2022.6

Symmetry-breaking charge separation in a nitrogen-bridged naphthalene monoimide dimer Reviewed International coauthorship International journal

Niu Xinmiao, Tajima Keita, Kong Jie, Tao Min, Fukui Norihito, Kuang Zhuoran, Shinokubo Hiroshi, Xia Andong

PHYSICAL CHEMISTRY CHEMICAL PHYSICS Vol. 24 ( 22 ) page： 14007 - 14015 2022.6

Synthesis and Tautomerization of 5-Azaporphyrinium Cations Reviewed International journal

Takiguchi Asahi, Shinokubo Hiroshi

Chemistry Letters Vol. 51 ( 6 ) page： 590 - 593 2022.6

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：The Chemical Society of Japan

Ring closure of 1-oxo-19-(phenylamino)bilin affords 5-azaporphyrinium cations. The introduction of a phenyl group on the meso-nitrogen induces a positive charge in the porphyrinic skeleton. Steric repulsion between the N-phenyl and β-ethyl substituents results in the deformation of the inner-cavity to a rectangle. The rectangular cavity and cationic charge induced the unique tautomerization of the inner-NH protons.

DOI： 10.1246/cl.220122

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Scopus

CiNii Research

5-Thiaporphyrinium cation: effect of sulphur incorporation on excited state dynamics Reviewed International coauthorship International journal

Asahi Takiguchi, Naoto Inai, Seongsoo Kang, Masaya Hagai, Seokwon Lee, Takeshi Yanai, Dongho Kim, Hiroshi Shinokubo

Chemical Communications Vol. 58 ( 40 ) page： 5956 - 5959 2022.5

Diverse Crystal Structures of Ion Pairs Consisting of Oxaporphyrinium Cations and Pentacyanocyclopentadienide Reviewed

Asahi Takiguchi, Hiroki Tanaka, Hiromitsu Maeda, Hiroshi Shinokubo

Bulletin of the Chemical Society of Japan Vol. 95 ( 5 ) page： 796 - 801 2022.3

Synthesis of Dibenzo[h,t]rubicene through Its Internally Dimethoxy-substituted Precursor Reviewed International journal

Kato, Masaki, Fukui, Norihito, Shinokubo, Hiroshi

Chemistry Letters Vol. 51 ( 3 ) page： 288 - 291 2022.3

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：The Chemical Society of Japan

Dibenzo[h,t]rubicene was synthesized from 1,5-dichloroanthraquinone via an internally dimethoxylated intermediate. In contrast to the planar conformation of rubicene, dibenzo[h,t]rubicene adopted a double-helicene-like structure due to the intramolecular steric repulsion around the fused benzene-rings. Theoretical calculation suggests that the helical inversion occurs frequently with an inversion barrier of 4.8 kcal mol−1. The HOMO–LUMO gap of dibenzo[h,t]rubicene is smaller than that of rubicene, resulting in its red-shifted absorption tailing to 690 nm.

DOI： 10.1246/cl.210754

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Nitrogen Extrusion of Diazacorrphycenes to Azacorroles and Synthesis of Two Types of Copper 10-Azacorrole Complexes Reviewed International journal

Yagi, Atsumi, Okada, Naoya, Fukui, Norihito, Tanaka, Hisaaki, Hatakeyama, Takuji, Shinokubo, Hiroshi

Chemistry Letters Vol. 51 ( 3 ) page： 321 - 324 2022.3

Authorship：Last author,　Corresponding author Language：Japanese Publishing type：Research paper (scientific journal) Publisher：The Chemical Society of Japan

The synthesis of Pd(II) and Cu(II) 10-azacorroles with a meso-NH group has been achieved through the thermal extrusion of one nitrogen atom from the corresponding diazacorrphycene metal complexes. We also found that oxidation of the Cu(II) 10-azacorrole complex afforded another type of copper 10-azacorrole with an imine moiety. The structural, magnetic, and electrochemical properties of these compounds were investigated to disclose the nature of two types of copper 10-azacorroles.

DOI： 10.1246/cl.210777

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A Heme-Acquisition Protein Reconstructed with a Cobalt 5-Oxaporphyrinium Cation and Its Growth-Inhibition Activity Toward Multidrug-Resistant Pseudomonas aeruginosa Reviewed International journal

Takiguchi Asahi, Sakakibara Erika, Sugimoto Hiroshi, Shoji Osami, Shinokubo Hiroshi

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 61 ( 7 ) page： e202112456 2022.2

Isolation and Structure Analysis of a Ni(II) Norcorrole Radical Anion Reviewed International journal

Ukai Shusaku, Fukui Norihito, Ikeue Takahisa, Shinokubo Hiroshi

Chemistry Letters Vol. 51 ( 2 ) page： 182 - 184 2022.2

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：The Chemical Society of Japan

A radical anion of Ni(II) meso-dimesitylnorcorrole was prepared and isolated upon chemical reduction of the corresponding neutral species with cobaltocene (CoIICp2). The radical anion was substantially stable under degassed solution conditions. X-ray crystal analysis of the radical anion revealed that the structural change by one-electron reduction is marginal. DFT calculations demonstrated that the reorganization energy of Ni(II) norcorrole upon one-electron reduction is smaller than those of Zn(II) porphyrin and C60 fullerenes.

DOI： 10.1246/cl.210715

A Supramolecular Polymer Constituted of Antiaromatic Ni(II) Norcorroles Reviewed International journal

Shusaku Ukai, Aiko Takamatsu, Masaki Nobuoka, Yusuke Tsutsui, Norihito Fukui, Soichiro Ogi, Shu Seki, Shigehiro Yamaguchi, Hiroshi Shinokubo

Angewandte Chemie International Edition Vol. 61 page： e202114230 2022.2

Indeno[1,2,3,4‐pqra ]Perylene: A Medium‐Sized Aromatic Hydrocarbon Exhibiting Full‐Range Visible‐Light Absorption Reviewed International journal

Masaki Kato, Norihito Fukui, Hiroshi Shinokubo

Chemistry – A European Journal Vol. 28 ( 2 ) page： e202103647 2022.1

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Wiley

We report the synthesis and properties of indeno[1,2,3,4-pqra]perylene, which was prepared by the fusion of one anthracene unit with one naphthalene unit via three carbon-carbon bonds. The synthetic route through two-fold C−H arylation enabled not only the synthesis of unsubstituted indenoperylene, but also rapid access to its arylated derivatives on the gram scale. Indenoperylene is a medium-sized aromatic hydrocarbon with the composition C24H12 that is isomeric to coronene. Nevertheless, its absorption covers the entire visible region owing to its small HOMO-LUMO gap. Furthermore, indenoperylene exhibits high stability despite the absence of peripheral substituents. We propose that the unique electronic structure of indenoperylene originates from the coexistence of an electron-withdrawing subunit (benzoaceanthrylene) and an electron-donating subunit (perylene). The electronic properties of indenoperylene were modulated via post-functionalization through regioselective bromination. The current research demonstrates that indenoperylene is a promising candidate as a main skeleton for near-infrared-responsive and redox-active materials.

DOI： 10.1002/chem.202103647

Other Link： https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chem.202103647

Dual-Ion NiNc Battery: A Sustainable Revolution for Sodium Organic Batteries Reviewed International journal

Jinkwang Hwang, Kazuhiko Matsumoto, Rika Hagiwara, Shusaku Ukai, Hiroshi Shinokubo, Ji-Young Shin

Batteries & Supercaps Vol. 4 ( 10 ) page： 1605 - 1610 2021.10

Manganese(III) 5,15-diazaporphyrins: Synthesis, properties, and catalytic use for benzylic C–H fluorination Reviewed International journal

Shiho Mori, Tsubasa Nishimura, Hiroshi Shinokubo, Yoshihiro Miyake

Journal of Porphyrins and Phthalocyanines Vol. 25 ( 10N12 ) page： 991 - 996 2021.10

Language：English Publishing type：Research paper (scientific journal) Publisher：World Scientific Pub Co Pte Lt

<jats:p> Fluorination of sp<jats:sup>3</jats:sup> C–H bonds has attracted considerable attention as a promising method for the synthesis of organofluorine compounds. Manganese porphyrins have been extensively investigated as catalysts in the fluorination of saturated sp<jats:sup>3</jats:sup> C–H bonds. Recently, we have found that iron(III) 5,15-diazaporphyrins, which are porphyrin analogues with imine-type sp<jats:sup>2</jats:sup>-hybridized nitrogen atoms at the meso-positions, showed high catalytic performance in the oxidation of sp<jats:sup>3</jats:sup> C–H bonds. Here we disclose the synthesis, structure, and electronic properties of manganese(III) 5,15-diazaporphyrins. We also demonstrate the catalysis of chloromanganese(III) 5,15-diazaporphyrins for benzylic fluorination. </jats:p>

DOI： 10.1142/S1088424621500887

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Antiaromatic 1,5‐Diaza‐ s ‐indacenes Reviewed International coauthorship International journal

Kensuke Hanida, Jinseok Kim, Norihito Fukui, Yusuke Tsutsui, Shu Seki, Dongho Kim, Hiroshi Shinokubo

Angewandte Chemie International Edition Vol. 60 ( 38 ) page： 20765 - 20770 2021.9

Synthesis of Tetrasilatetrathia[8]circulenes through C-I and C-H Silylation Invited Reviewed International journal

Akahori Shuhei, Fujihara Tetsuaki, Tsuji Yasushi, Shinokubo Hiroshi, Miyake Yoshihiro

Vol. 53 ( 17 ) page： 2995 - 3000 2021.9

Determinant Factors of Three-Dimensional Aromaticity in Antiaromatic Cyclophanes Reviewed International coauthorship International journal

Hiroyuki Kawashima, Shusaku Ukai, Ryo Nozawa, Norihito Fukui, Garrett Fitzsimmons, Tim Kowalczyk, Heike Fliegl, Hiroshi Shinokubo

Journal of the American Chemical Society Vol. 143 ( 28 ) page： 10676 - 10685 2021.7

Non‐Planar Perylene Bisimide Analogues with Inserted Carbonyl and Methylene Subunits Reviewed International journal

Mai Odajima, Keita Tajima, Norihito Fukui, Hiroshi Shinokubo

Angewandte Chemie International Edition Vol. 60 ( 29 ) page： 15838 - 15843 2021.7

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Wiley

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

Acridino[2,1,9,8‐ klmna ]acridine Bisimides: An Electron‐Deficient π‐System for Robust Radical Anions and n‐Type Organic Semiconductors Reviewed International journal

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

Angewandte Chemie International Edition Vol. 60 ( 25 ) page： 14060 - 14067 2021.6

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Wiley

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

Synthesis and Characterization of 16 pi Antiaromatic 2,7-Dihydrodiazapyrenes: Antiaromatic Polycyclic Hydrocarbons with Embedded Nitrogen Reviewed International journal

Nakazato, Takumi, Takekoshi, Haruka, Sakurai, Takahiro, Shinokubo, Hiroshi, Miyake, Yoshihiro

Angewandte Chemie International Edition Vol. 60 ( 25 ) page： 13877 - 13881 2021.6

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Papers - SHINOKUBO, Hiroshi