Faculty Profiles - SHINOKUBO, Hiroshi

Papers - SHINOKUBO, Hiroshi

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Ultrafine Spatial Modulation of Diazapyrene-Based Two-Dimensional Conjugated Covalent Organic Frameworks Reviewed International coauthorship International journal

Zhuowei Li, Takahiro Tsuneyuki, Rajendra Prasad Paitandi, Takumi Nakazato, Masahiro Odawara, Yusuke Tsutsui, Takayuki Tanaka, Yoshihiro Miyake, Hiroshi Shinokubo, Makito Takagi, Tomomi Shimazaki, Masanori Tachikawa, Katsuaki Suzuki, Hironori Kaji, Samrat Ghosh, Shu Seki

Journal of the American Chemical Society Vol. 146 ( 33 ) page： 23497 - 23507 2024.8

Homochiral and Heterochiral Self‐Sorting Assemblies of Antiaromatic Ni(II) Norcorrole Dimers Reviewed International journal

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

Chemistry – A European Journal Vol. 30 ( 39 ) page： e202400292 2024.7

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

Synthesis of sterically congested double helicene by alkyne cycloisomerization Invited Reviewed International journal

Junichiro Hirano, Sayaka Miyoshi, Eiji Yashima, Tomoyuki Ikai, Hiroshi Shinokubo, Norihito Fukui

Chemical Communications Vol. 60 ( 47 ) page： 6035 - 6038 2024.6

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

Alkyne cycloisomerization of 2,7,10,15-tetra(ortho-alkynylphenyl)benzo[g,p]chrysene containing bulky 4-alkoxy-2,6-dimethylphenyl groups at the alkyne terminals selectively proceeded at the sterically crowded bay-region.

DOI： 10.1039/d4cc01573h

End-to-End Bent Perylene Bisimide Cyclophanes by Double Sulfur Extrusion Reviewed International journal

Yuki Tanaka, Keita Tajima, Ryota Kusumoto, Yasuhiro Kobori, Norihito Fukui, Hiroshi Shinokubo

Journal of the American Chemical Society Vol. 146 ( 23 ) page： 16332 - 16339 2024.5

Norcorroles as antiaromatic π-electronic systems that form dimension-controlled assemblies Reviewed International journal

Soh Ishikawa, Kazuhisa Yamasumi, Shinya Sugiura, Shunsuke Sato, Go Watanabe, Yun Hee Koo, Shu Seki, Yuya Bando, Yohei Haketa, Hiroshi Shinokubo, Hiromitsu Maeda

Chemical Science Vol. 15 ( 20 ) page： 7603 - 7609 2024.5

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

Norcorroles with 3,4,5-trialkoxyphenyl moieties were synthesized to form thermotropic liquid crystals (LCs), in which triple-decker stacking structures were formed. The LC state exhibited discotic columnar structures to exhibit high electric conductivity.

DOI： 10.1039/d4sc01633e

Changing aromatic properties through stacking: the face-to-face dimer of Ni(II) bis(pentafluorophenyl)norcorrole Reviewed International coauthorship International journal

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

Physical Chemistry Chemical Physics Vol. 26 ( 20 ) page： 14777 - 14786 2024.5

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

The diatropic (red) and paratropic (yellow) current density of the antiaromatic Ni(ii) bis(pentafluorophenyl)norcorrole and of its aromatic face-to-face stacked dimer.

DOI： 10.1039/d4cp00968a

Inner-bond-cleavage approach to figure-eight macrocycles from planar aromatic hydrocarbons Reviewed International journal

Reiji Yoshina, Junichiro Hirano, Emiko Nishimoto, Yuki Sakamoto, Keita Tajima, Shunsuke Minabe, Muhammet Uyanik, Kazuaki Ishihara, Tomoyuki Ikai, Eiji Yashima, Takuya Omine, Fumitaka Ishiwari, Akinori Saeki, Jinseok Kim, Juwon Oh, Dongho Kim, Guanting Liu, Takuma Yasuda, Hiroshi Shinokubo, Norihito Fukui

Journal of the American Chemical Society Vol. 146 page： 29383 - 29390 2024.5

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

<jats:p>Contemporary synthetic strategies in organic chemistry rely heavily on the stepwise formation of bonds between fragments of the target compound (‘bottom-up’ approach). Figure-eight aromatic macrocycles represent a considerable challenge for the bottom-up approach, and the lack of versatile synthetic routes to such macrocycles prevents the use of their distinctive chiral D2-symmetric structures in advanced materials. Herein, we demonstrate the oxidative cleavage of internal double bonds of planar polycyclic aromatic hydrocarbons enables the scalable, catalytic, and enantioselective synthesis of figure-eight macrocycles. These macrocycles, with incorporated carbonyl groups, serve as a chiral electron-acceptor unit to furnish a thermally activated delayed fluorescence material with efficient circularly polarized luminescence. The inner-bond-cleavage approach is thus an effective alternative to the bottom-up approach, proving access to hitherto inaccessible materials.</jats:p>

DOI： 10.26434/chemrxiv-2024-j1xxr

CiNii Research

Triply-Linked Porphyrin−Norcorrole Hybrid with Singlet Diradical Character Reviewed International coauthorship International journal

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

Angewandte Chemie International Edition Vol. 63 ( 16 ) page： e202401233 2024.4

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

Norcorrole Ni(II) complexes have recently received considerable attention as readily accessible antiaromatic molecules. Their high stabil-ity under ambient conditions and easy synthesis have enabled the exploration of the intrinsic properties of antiaromatic molecules. Here, we report the synthesis and properties of directly meso−meso singly-linked porphyrin−norcorrole hybrids and triply-linked porphy-rin−norcorrole hybrids. The singly-linked and triply-linked porphyrin−norcorrole hybrids were fully characterized, including their X-ray structural analysis. Because of their orthogonal conformation, singly-linked hybrids maintained the individual electronic property of por-phyrin and norcorrole subunits The triply-linked hybrid showed a significant decrease in the HOMO–LUMO gaps, the paratropic ring current in the norcorrole subunit, and the diamagnetic ring current in the porphyrin subunit. Furthermore, the triply-linked hybrid exhib-ited singlet diradical characteristics, confirmed by VT-NMR, ESR, and SQUID experiments.

DOI： 10.1002/anie.202401233

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

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Papers - SHINOKUBO, Hiroshi