研究者詳細 - 西原　康師

論文 - 西原　康師

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

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

Journal of Polymer Science 2024年11月

掲載種別：研究論文（学術雑誌）出版者・発行元：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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その他リンク： 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) 招待査読

Tian Tian, Shuhei Uei, Zhiping Li, Yasushi Nishihara

ChemCatChem 2024年9月

担当区分：最終著者,　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

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 査読

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

Chemical Communications 60 ( 79 ) 11152 - 11155 2024年9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：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

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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 査読

Tian Tian, Myuto Kashihara, Weidan Yan, Yasushi Nishihara

ACS Catalysis 14 ( 16 ) 11905 - 11917 2024年7月

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

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

ACS Applied Polymer Materials 6 ( 7 ) 3883 - 3893 2024年3月

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

Hiroki Mori, Natsuki Hasegawa, Tomoki Yoshino, Yasushi Nishihara

Chemistry Letters 52 ( 10 ) 779 - 782 2023年10月

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

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

The Journal of Organic Chemistry 88 ( 7 ) 4472 - 4480 2023年3月

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

Hiroki Mori, Yuya Asanuma, Ryuchi Hosogi, Yasushi Nishihara

Polymer Journal 55 ( 4 ) 405 - 415 2023年1月

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

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

Organic Letters 24 ( 50 ) 9259 - 9263 2022年12月

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

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年7月

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

Tian Tian, Qiang Chen, Zhiping Li, Yasushi Nishihara

Synthesis 54 ( 17 ) 3667 - 3697 2022年5月

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

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

Bulletin of Chemical Society of Japan 95 ( 6 ) 942 - 952 2022年4月

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

Qiang Chen, Zhenyao Li, Yasushi Nishihara

Organic Letters 24 ( 1 ) 385 - 389 2022年1月

Transmetalation of boronic acids and their derivatives: mechanistic elucidation and relevance to catalysis 招待査読

Kohtaro Osakada, Yasushi Nishihara

Dalton Transactions 51 ( 3 ) 777 - 794 2021年12月

Ni-Catalyzed Decarbonylative Alkynylation of Acyl Fluorides with Terminal Alkynes under Copper-Free Conditions 招待査読

Qiang Chen, Liyan Fu, Jingwen You, Yasushi Nishihara

Synlett 32 ( 15 ) 1560 - 1564 2021年10月

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

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

Chemical Communications 57 ( 73 ) 9276 - 9279 2021年8月

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

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年7月

Nickel-Catalyzed Decarbonylative Thioetherification of Acyl Fluorides via C-F Bond Activation 招待査読

Jingwen You, Qiang Chen, Yasushi Nishihara

Synthesis 53 ( 17 ) 3045 - 3050 2021年4月

Recent Advances in Transition-metal-catalyzed C-C Bond Formation via C(sp2)-F Bond Cleavage 査読

Liyan Fu, Qiang Chen, Yasushi Nishihara

Chemical Records 21 ( 12 ) 3394 - 3410 2021年4月

Palladium-catalyzed decarbonylative and decarboxylative cross-coupling of acyl chlorides with potassium perfluorobenzoates affording unsymmetrical biaryls 査読

Liyan Fu, Jingwen You, Yasushi Nishihara

Chemical Communications 57 ( 30 ) 3696 - 3699 2021年3月

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