Electron-Accepting π-Conjugated Compound Containing Cyano-Substituted Naphthobisthiadiazole as Nonfullerene Acceptor in Organic Solar Cells

Seihou Jinnai; Ayumi Oi; Takuji Seo; Taichi Moriyama; Ryunosuke Minami; Suguru Higashida; Yutaka Ie

doi:10.1055/a-1528-1632

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(18): 3390-3396
DOI: 10.1055/a-1528-1632

special topic

Bond Activation – in Honor of Prof. Shinji Murai

Electron-Accepting π-Conjugated Compound Containing Cyano-Substituted Naphthobisthiadiazole as Nonfullerene Acceptor in Organic Solar Cells

Seihou Jinnai

^aThe Institute of Scientific and Industrial Research (SANKEN), Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka 567-0047, Japan

,

Ayumi Oi

^aThe Institute of Scientific and Industrial Research (SANKEN), Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka 567-0047, Japan

,

Takuji Seo

^aThe Institute of Scientific and Industrial Research (SANKEN), Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka 567-0047, Japan

,

Taichi Moriyama

^bIshihara Sangyo Kaisha, Ltd., 3-1 Nishi-shibukawa 2-chome, Kusatsu, Shiga 525-0025, Japan

,

Ryunosuke Minami

^cOsaka Prefecture University College of Technology, 26-12 Saiwai, Neyagawa, Osaka 572-8572, Japan

,

Suguru Higashida

^cOsaka Prefecture University College of Technology, 26-12 Saiwai, Neyagawa, Osaka 572-8572, Japan

,

Yutaka Ie ∗

^aThe Institute of Scientific and Industrial Research (SANKEN), Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka 567-0047, Japan

^dInnovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (OTRI), Osaka University, Japan

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Abstract

Alle Artikel dieser Rubrik

This manuscript is dedicated to Professor Shinji Murai in honor of his pioneering C–H activation research.

Abstract

The incorporation of electron-accepting units into π-conjugated systems can allow the modulation of the physical properties and frontier orbital energy levels of the molecules. An electron-accepting π-conjugated compound (CNNTz-TR) containing cyano-substituted naphthobisthiadiazole (CNNTz) was synthesized via a nucleophilic substitution reaction as the key step. Owing to the presence of the cyano groups, CNNTz-TR affords a low-lying lowest unoccupied molecular orbital energy level. Organic solar cells based on the blend films of CNNTz-TR and a low-bandgap donor exhibited moderate power conversion efficiencies. The results showed that embedding the CNNTz unit into the π-conjugated backbone is an effective approach for designing electron-accepting semiconducting materials.

Key words

naphthobisthiadiazoles - organic solar cells - nonfullerene acceptors - π-conjugated molecules - organic semiconducting materials - electron-accepting unit

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