Faculty Profiles - SHINOKUBO, Hiroshi

Papers - SHINOKUBO, Hiroshi

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Close Stacking of Antiaromatic Ni(II) Norcorrole Originating from a Four-Electron Multicentered Bonding Interaction Reviewed International coauthorship International journal

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 Vol. 146 ( 13 ) page： 9311 - 9317 2024.3

Interaction strength in molecular junctions consisting of π-stacked antiaromatic molecules Reviewed International journal

Shintaro Fujii, Ryoya Tomida, Aoshi Yamane, Kazuki Nabeyama, Harunari Ohkura, Hiroshi Shinokubo, Tomoaki Nishino

Journal of Materials Chemistry C Vol. 12 ( 5 ) page： 1640 - 1643 2024.2

Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Royal Society of Chemistry (RSC)

The interaction force was measured as the adhesive force acting between norcorrole molecules anchored to the probe surface and the sample surface. This study reveals substantial interactions in π-stacked antiaromatics at the single-molecule scale.

DOI： 10.1039/d3tc04166b

Excimer Formation Driven by Excited-State Structural Relaxation in a Covalent Aminonaphthalimide Dimer Reviewed International coauthorship International journal

Rui Jing, Yang Li, Keita Tajima, Yan Wan, Norihito Fukui, Hiroshi Shinokubo, Zhuoran Kuang, Andong Xia

The Journal of Physical Chemistry Letters Vol. 15 ( 5 ) page： 1469 - 1476 2024.1

Synthesis and properties of bay-functionalized 9,9′-bifluorenylidene derivatives Reviewed International journal

Junichiro Hirano, Hiroshi Shinokubo, Norihito Fukui

Chemistry Letters Vol. 53 ( 1 ) page： upad015 2024.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Oxford University Press (OUP)

Abstract

Here, we disclose the effect of substitution at the bay-region of 9,9′-bifluorenylidene on its optical and electrochemical properties. Bay-brominated 9,9′-bifluorenylidene was synthesized by the reductive dimerization of 4,5-dibromofluorenone with triethyl phosphite. The subsequent Suzuki–Miyaura cross-coupling afforded arylated derivatives. X-ray diffraction analysis revealed that the bulky bay-substituents twist the overall structure through the relay of the steric repulsion from the bay-region to the fjord-region. The π-extension at the bay-region with tolyl and 4-dimethylaminophenyl groups increases the electron-donating ability, while the introduction of bromo groups enhances the electron-accepting ability.

DOI： 10.1093/chemle/upad015

Other Link： https://academic.oup.com/chemlett/article-pdf/53/1/upad015/56961460/upad015.pdf

Syntheses of Thiophene–Thiophene-Linked Corrorin Dimers with Tunable Near-Infrared Absorption and Distinctive Reactivity Reviewed International coauthorship International journal

Yue Xu, Bin Zhu, Lingfang Zhang, Glib Baryshnikov, Feng Sha, Emiko Nishimoto, Hideaki Takano, Chengjie Li, Xinyan Wu, Hans Ågren, Hiroshi Shinokubo, Yongshu Xie, Qizhao Li

Organic Letters Vol. 26 ( 2 ) page： 571 - 576 2024.1

Metallaantiaromaticity of 10-Platinacorrole Complexes Reviewed International coauthorship International journal

Kazuki Miwa, Tomoya Yokota, Qian Wang, Takahiro Sakurai, Heike Fliegl, Dage Sundholm, Hiroshi Shinokubo

Journal of the American Chemical Society Vol. 146 ( 2 ) page： 1396 - 1402 2024.1

Effect of Internal Substituents on the Properties of Dibenzo[g,p]chrysene Reviewed International journal

Yoshihiro Takeo, Junichiro Hirano, Norihito Fukui, Hiroshi Shinokubo

Organic Letters Vol. 25 ( 47 ) page： 8484 - 8488 2023.11

Effect of internal oxygen substituents on the properties of bowl-shaped aromatic hydrocarbons Reviewed International journal

Takeo, Y; Hirano, J; Shimizu, D; Fukui, N; Shinokubo, H

ORGANIC CHEMISTRY FRONTIERS Vol. 10 page： 5895 - 5901 2023.10

Intrinsic Photostability in Dithiolonaphthalimide Achieved by Disulfide Bond-Induced Excited-State Quenching Reviewed International coauthorship International journal

Zeming Wang, Rui Jing, Yang Li, Di Song, Yan Wan, Norihito Fukui, Hiroshi Shinokubo, Zhuoran Kuang, Andong Xia

The Journal of Physical Chemistry Letters Vol. 14 ( 38 ) page： 8485 - 8492 2023.9

Unique solvent effect of water in radical cyclization reaction Reviewed International journal

Sara Suzuki, Soni Aman Govind, Kosuke Imamura, Hideki Yorimitsu, Hiroshi Shinokubo, Masahiro Higashi, Hirofumi Sato

Chemical Physics Letters Vol. 826 page： 140641 2023.9

Easily Switchable 18π‐, 19π‐, and 20π‐Conjugation of Diazaporphyrin Double‐Pincer Bispalladium Complexes Reviewed International journal

Takahiro Sakurai, Yuya Hiraoka, Hisaaki Tanaka, Yoshihiro Miyake, Norihito Fukui, Hiroshi Shinokubo

Angewandte Chemie International Edition Vol. 62 ( 12 ) page： e202300437 2023.2

Near‐Infrared‐Responsive Hydrocarbons Designed by π‐Extension of Indeno[1,2,3,4‐pgra]perylene at the 1,2,12‐Positions Reviewed International coauthorship International journal

Masaki Kato, Jinseok Kim, Juwon Oh, Daiki Shimizu, Norihito Fukui, Hiroshi Shinokubo

Chemistry – A European Journal 2023.1

Dinaphthooxepine Bisimide Undergoes Oxygen Extrusion Reaction upon Electron Injection at Room Temperature Reviewed International journal

Mai Odajima, Norihito Fukui, Hiroshi Shinokubo

Organic Letters Vol. 25 ( 1 ) page： 282 - 287 2023.1

One-dimensional stacking array of 10,20-diphenyl-5,15-diazaporphyrin metal complexes Invited Reviewed International journal

Shiho Mori, Takahiro Sakurai, Tsubasa Nishimura, Norihito Fukui, Yoshihiro Miyake, Hiroshi Shinokubo

Journal of Porphyrins and Phthalocyanines Vol. 27 page： 1035 - 1041 2023.1

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：World Scientific Pub Co Pte Ltd

We prepared a free-base 10,20-diphenyl-5,15-diazaporphyrin and its Ni(II), Cu(II), Pd(II), and Pt(II) complexes. These molecules uniformly form an infinite one-dimensional [Formula: see text]-stacking array in the solid state. The four-fold intermolecular hydrogen bonding interactions between the meso-nitrogen atom of the diazaporphyrin core and the ortho-hydrogen atom of the phenyl substituent dominate the crystal packing arrangement. The present study revealed that the meso-nitrogen atom of diazaporphyrins would be used as an inherent hydrogen bonding acceptor to construct supramolecular assemblies.

DOI： 10.1142/s1088424622500997

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Diazazethrene bisimide: a strongly electron-accepting π-system synthesized <i>via</i> the incorporation of both imide substituents and imine-type nitrogen atoms into zethrene Reviewed International journal

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

Chemical Science Vol. 14 ( 3 ) page： 635 - 642 2022.12

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Royal Society of Chemistry (RSC)

The development of highly electron-accepting π-systems is a fundamentally challenging issue despite their potential applications as various functional materials.

DOI： 10.1039/d2sc05992d

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Highly soluble Ni(II) dithienylnorcorrole Invited Reviewed International coauthorship International journal

Shiori Itabuchi, Ryo Nozawa, Takuya Yoshida, Norihito Fukui, Hiroshi Shinokubo

Journal of Porphyrins and Phthalocyanines page： A - E 2022.11

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：World Scientific Pub Co Pte Ltd

Recently, norcorrole Ni(II) complexes have received much attention because they exhibit peculiar solid-state structures and fascinating electronic properties originating from their distinct antiaromatic character. In this work, we have prepared a norcorrole Ni(II) complex with 5-hexylthien-2-yl substituents at the meso-positions, of which the antiaromatic nature was evaluated by <sup>1</sup>H NMR analysis as well as NICS and ACID calculations. The X-ray diffraction analysis elucidated its molecular structure and crystal packing arrangement. Crystal packing structures of Ni(II) meso-di(5-methylthien-2-yl)norcorrole and Ni(II) meso-di(5-hexylthien-2-yl)norcorrole were markedly different. The latter provided a polar crystal because of the unidirectional alignment of 5-hexylthien-2-yl groups in the solid state.

DOI： 10.1142/S1088424622500730

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Realization of Stacked-Ring Aromaticity in a Water-Soluble Micellar Capsule Reviewed International coauthorship International journal

Si-Yu Liu, Natsuki Kishida, Jinseok Kim, Norihito Fukui, Rie Haruki, Yasuhiro Niwa, Reiji Kumai, Dongho Kim, Michito Yoshizawa, Hiroshi Shinokubo

Journal of the American Chemical Society Vol. 145 ( 4 ) page： 2135 - 2141 2022.10

Planarization of a bowl-shaped molecule by triple-decker stacking Reviewed International journal

Hiroyuki Kawashima, Norihito Fukui, Quan Manh Phung, Takeshi Yanai, Hiroshi Shinokubo

Cell Reports Physical Science Vol. 3 ( 9 ) page： 101045 - 101045 2022.9

d-Mannose-appended 5,15-diazaporphyrin for photodynamic therapy Reviewed International coauthorship International journal

Ali Lamiaa M. A., Miyagawa Kazuya, Fukui Norihito, Onofre Melanie, El Cheikh Khaled, Morere Alain, Clement Sebastien, Gary-Bobo Magali, Richeter Sebastien, Shinokubo Hiroshi

ORGANIC & BIOMOLECULAR CHEMISTRY 2022.8

Gram-Scale Diversity-Oriented Synthesis of Dinaphthothiepine Bisimides as Soluble Precursors for Perylene Bisimides Reviewed International journal

Tanaka Yuki, Matsuo Kyohei, Yamada Hiroko, Fukui Norihito, Shinokubo Hiroshi

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY Vol. 2022 ( 31 ) 2022.8

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Papers - SHINOKUBO, Hiroshi