Faculty Profiles - NISHIHARA Yasushi

Papers - NISHIHARA Yasushi

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From carboxylic acids or their derivatives to amines and ethers: modern decarboxylative approaches for sustainable C-N and C-O bond formation. Reviewed International journal

Weidan Yan, Tian Tian, Yasushi Nishihara

Organic & biomolecular chemistry 2025.7

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

Amines and ethers represent essential structural motifs in pharmaceuticals, natural products, organic materials, and catalytic systems. The development of novel, environmentally friendly, and cost-effective strategies for constructing C-N and C-O bonds is therefore of significant importance for the synthesis of these compounds. In recent years, carboxylic acids and their derivatives have emerged as attractive, inexpensive, non-toxic, and readily available synthetic building blocks, serving as promising alternatives to aryl halides. Growing evidence has demonstrated that decarboxylative amination and etherification of carboxylic acid derivatives offer a powerful approach for the synthesis of amines and ethers. These transformations proceed via three principal mechanistic pathways, each offering high atom economy. Specifically, carbanions (or organometallic species) generated through heterolytic decarboxylation can react with suitable electrophiles to form C-heteroatom bonds. In contrast, carbon-centred radicals produced through homolytic decarboxylation can couple with heteroatom-based reagents via radical recombination or oxidative trapping. Additionally, carbocations are typically formed via electrochemical oxidation of carboxylic acids: oxidative decarboxylation first yields a carbon radical, which is then further oxidized at the anode to generate a carbocation. This highly electrophilic intermediate can subsequently be intercepted by heteroatom nucleophiles to construct C-N or C-O bonds. This review highlights recent advances in the field, with a focus on transition metal catalysis, photoredox catalysis, and electrochemical methods for decarboxylative amination and etherification.

DOI： 10.1039/d5ob00748h

PubMed

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Alkoxy-Substituted Anthrabis(Thiadiazole)-Terthiophene Copolymers for Organic Photovoltaics: A Unique Wavy Backbone Enhances Aggregation, Molecular Order, and Device Efficiency. Reviewed International journal

Yi Yan, Hiroki Mori, Tomoki Yoshino, Ryuki Inami, Jiaxin Chang, Junqing Gao, Yasushi Nishihara

Chemistry, an Asian journal e00678 2025.6

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

Two polymer donors, PATz3T-o6BO and PATz3T-o6HD, incorporating alkoxy-substituted anthra[1,2-c:5,6-c']bis([1,2,5]thiadiazole), were strategically designed and synthesized. The unique wavy backbone of these polymers effectively reduced aggregation, leading to enhanced solubility and significantly improved molecular ordering. Consequently, the PATz3T-o6HD:Y12-based solar cells achieved a power conversion efficiency (PCE) of 7.94%. These findings provide valuable insights into the molecular design of high-performance polymer donors for organic photovoltaics (OPVs).

DOI： 10.1002/asia.202500678

PubMed

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Vinylene‐Bridged Alkoxyfluorobenzothiadiazole (<scp>FOBTzE</scp>)‐Based Semiconducting Polymers for Enhanced Performance in Non‐Fullerene Organic Photovoltaic Cells Reviewed

Yi Yan, Hiroki Mori, Ryuchi Hosogi, Hiroki Yamane, Tomoki Yoshino, Yasushi Nishihara

Journal of Polymer Science 2024.11

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

ABSTRACT

To mitigate the strong aggregation and limited solubility observed in the previously reported vinylene‐bridged alkoxyfluorobenzothiadiazole (FOBTzE)‐based polymer, PFOE4T, we designed and synthesized PBFOE‐1. This novel semiconducting polymer, based on the FOBTzE framework, incorporates an alkylthienyl‐substituted benzodithiophene (BDT) as the donor unit. PBFOE‐1 demonstrated broad and intense absorption between 300 and 700 nm with a relatively wide bandgap of 1.7 eV. Additionally, PBFOE‐1 features a low HOMO energy level (−5.43 eV) compared to PFOE4T (−5.23 eV), likely due to the incorporation of weakly electron‐donating BDT into the polymer backbone. While the PFOE4T/Y12‐based solar cell yielded a modest power conversion efficiency (PCE) of 4.37%, characterized by a short‐circuit current density (J_sc) of 13.5 mA cm⁻², an open‐circuit voltage (V_oc) of 0.69 V, and a fill factor (FF) of 0.47, the PBFOE‐1/Y12 cell exhibited a substantially higher PCE of 10.96%. This improvement is reflected in the enhanced J_sc (23.23 mA cm⁻²), V_oc (0.84 V), and FF (0.56). The superior performance of PBFOE‐1 is primarily attributed to its improved solubility and aggregation behavior, promoting a more ordered face‐on orientation and optimal blend morphology.

DOI： 10.1002/pol.20241036

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Other Link： https://onlinelibrary.wiley.com/doi/pdf/10.1002/pol.20241036

A Highly Efficient Cross‐Coupling Mode via the Release of Small Molecules: Transition Metal‐Catalyzed Unimolecular Fragment Coupling (UFC) Invited Reviewed

Tian Tian, Shuhei Uei, Zhiping Li, Yasushi Nishihara

ChemCatChem 2024.9

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

Abstract

As a recently developed redox‐neutral coupling reaction, transition‐metal‐catalyzed unimolecular fragment coupling (UFC) has been extensively investigated over the past decade. In comparison to conventional cross‐coupling reactions, cross‐electrophilic coupling (XEC) and cross‐dehydrogenative coupling (CDC) protocols eliminate the need for stoichiometric organometallic reagents, reductants, or oxidants. Additionally, it produces only minimal molecular by‐products for the formation of a series of C−C bonds and C−X bonds with high atom efficiency. This review presents a summary and classification of the research progress made over the past decade in this field. The research is classified into four main categories, decarbonylation, decarboxylation, desulfonylation, and deisocyanation, according to the type of small molecule that is liberated from the reaction system. This facilitates the implementation of more practical, straightforward, and expedient reaction operations. It is noteworthy that the reaction employs carbonyl compounds (aldehydes, ketones, carboxylic acid derivatives, etc.), sulfones, and amides, which are typically inexpensive and accessible, as reaction substrates. This groundbreaking synthetic approach has since yielded a plethora of outcomes and novel research avenues in related fields, while also offering benefits to other related fields.

DOI： 10.1002/cctc.202401190

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Thiophene-fused fulminenes (FuDTs): promising platforms for high-mobility organic semiconductors with a zigzag shape Reviewed International journal

Shohei Kumagai, Takumi Ishida, Shin Kakiuchi, Masakazu Yamagishi, Hiroyasu Sato, Hiroyuki Ishii, Yasushi Nishihara, Toshihiro Okamoto

Chemical Communications 60 ( 79 ) 11152 - 11155 2024.9

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

[8]Thienophenacene analogues offer excellent single-crystal platforms for hole transport owing to their characteristic molecular orbitals and sufficiently small effective masses.

DOI： 10.1039/d4cc02767a

PubMed

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Palladium-Catalyzed Decarbonylative Nucleophilic Halogenation of Acyl Fluorides and Chlorides: Synthesis of Aryl Halides via Reductive Elimination of the C–X (X = I, Br, and Cl) Bond and Mechanistic Implications Reviewed

Tian Tian, Myuto Kashihara, Weidan Yan, Yasushi Nishihara

ACS Catalysis 14 ( 16 ) 11905 - 11917 2024.7

Alkoxy-Substituted Anthrabisthiadiazole–Benzodithiophene-Based Wide-Band-Gap Semiconducting Polymers for High-Performance Non-Fullerene Solar Cells Reviewed

Hiroki Mori, Ryuchi Hosogi, Yukiya Minagawa, Hiroki Yamane, Yasushi Nishihara

ACS Applied Polymer Materials 6 ( 7 ) 3883 - 3893 2024.3

Synthesis, Characterization, and Solar Cell Applications of a Non-fused-ring Electron Acceptor Based on Vinylene-bridged Difluorobenzothiadiazole Reviewed

Hiroki Mori, Natsuki Hasegawa, Tomoki Yoshino, Yasushi Nishihara

Chemistry Letters 52 ( 10 ) 779 - 782 2023.10

Carboazidation of Terminal Alkenes with Trimethylsilyl Azide and Cyclic Ethers Catalyzed by Copper Powder under Oxidative Conditions Reviewed

Yuichi Ikemoto, Sho Chiba, Zhenyao Li, Qiang Chen, Hiroki Mori, Yasushi Nishihara

The Journal of Organic Chemistry 88 ( 7 ) 4472 - 4480 2023.3

Synthesis and solar cell applications of semiconducting polymers based on vinylene-bridged 5-alkoxy-6-fluorobenzo[c][1,2,5]thiadiazole (FOBTzE) Reviewed

Hiroki Mori, Yuya Asanuma, Ryuchi Hosogi, Yasushi Nishihara

Polymer Journal 55 ( 4 ) 405 - 415 2023.1

Nickel-Catalyzed Decarbonylative Reductive Alkylation of Aroyl Fluorides with Alkyl Bromides Reviewed

Qiang Chen, Jingwen You, Tian Tian, Zhenyao Li, Myuto Kashihara, Hiroki Mori, Yasushi Nishihara

Organic Letters 24 ( 50 ) 9259 - 9263 2022.12

π-Extended Zigzag-Shaped Diphenanthrene-Based p-Type Semiconductors Exhibiting Small Effective Masses Reviewed

Masato Mitani, Shohei Kumagai, Craig P. Yu, Ayako Oi, Masakazu Yamagishi, Shuhei Nishinaga, Hiroki Mori, Yasushi Nishihara, Daisuke Hashizume, Tadanori Kurosawa, Hiroyuki Ishii, Nobuhiko Kobayashi, Jun Takeya, Toshihiro Okamoto

Advanced Electronic Materials 8 ( 11 ) 2200452 - 2200452 2022.7

Recent Advances in C-F Bond Activation of Acyl Fluorides Directed toward Catalytic Transformation by Transition Metals, N-Heterocyclic Carbenes, or Phosphines Invited Reviewed

Tian Tian, Qiang Chen, Zhiping Li, Yasushi Nishihara

Synthesis 54 ( 17 ) 3667 - 3697 2022.5

Effects of Acyloxy Groups in Anthrabisthiadiazole-Based Semiconducting Polymers on Electronic Properties, Thin-Film Structure, and Solar Cell Performance Reviewed

Hiroki Mori, Yuki Yamada, Yukiya Minagawa, Natsuki Hasegawa, Yasushi Nishihara

Bulletin of Chemical Society of Japan 95 ( 6 ) 942 - 952 2022.4

Palladium/Copper-Cocatalyzed Arylsilylation of Internal Alkynes with Acyl Fluorides and Silylboranes: Synthesis of Tetrasubstituted Alkenylsilanes by Three-Component Reviewed

Qiang Chen, Zhenyao Li, Yasushi Nishihara

Organic Letters 24 ( 1 ) 385 - 389 2022.1

Transmetalation of boronic acids and their derivatives: mechanistic elucidation and relevance to catalysis Invited Reviewed

Kohtaro Osakada, Yasushi Nishihara

Dalton Transactions 51 ( 3 ) 777 - 794 2021.12

Ni-Catalyzed Decarbonylative Alkynylation of Acyl Fluorides with Terminal Alkynes under Copper-Free Conditions Invited Reviewed

Qiang Chen, Liyan Fu, Jingwen You, Yasushi Nishihara

Synlett 32 ( 15 ) 1560 - 1564 2021.10

Iron-catalysed radical cyclization to synthesize germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones Reviewed

Yani Luo, Tian Tian, Yasushi Nishihara, Leiyang Lv, Zhiping Li

Chemical Communications 57 ( 73 ) 9276 - 9279 2021.8

Formation of trans-Poly(thienylenevinylene) Thin Films by Solid-State Thermal Isomerization Reviewed

Masayuki Wakioka, Natsumi Yamashita, Hiroki Mori, Richard Murdey, Takafumi Shimoaka, Nobutaka Shioya, Atsushi Wakamiya, Yasushi Nishihara, Takeshi Hasegawa, Fumiyuki Ozawa

Chemistry of Materials 33 ( 14 ) 5631 - 5638 2021.7

Nickel-Catalyzed Decarbonylative Thioetherification of Acyl Fluorides via C-F Bond Activation Invited Reviewed

Jingwen You, Qiang Chen, Yasushi Nishihara

Synthesis 53 ( 17 ) 3045 - 3050 2021.4

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Papers - NISHIHARA Yasushi