期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 143, 期 9, 页码 3306-3311出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c00189
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资金
- JSPS KAKENHI [JP19K15528, JP20H02719, JP20K21184]
Octaaryl-substituted bisquinodimethanes (BQDs) with a zigzag structure were designed as redox-switchable molecules that can undergo four-electron oxidation to produce tetracationic pentacenes with a doubly twisted structure. By stepwise two-electron reduction, the tetracationic pentacenes can be transformed into dicationic anthracenes and then back to the original BQDs. The structures and UV-vis-NIR spectra of these molecules can be controlled by redox stimuli, as they exhibit near-infrared absorptions based on an intramolecular charge-transfer interaction.
Octaaryl-substituted bisquinodimethanes (BQDs) with a zigzag structure were designed as redox-switchable molecules that undergo four-electron oxidation to produce tetracationic pentacenes with a doubly twisted structure. In contrast to one-stage four-electron oxidation of BQDs, stepwise two-electron reduction of tetracationic pentacenes occurs to give dicationic anthracenes and then the original BQDs, step-by-step. Since both tetracations and dications exhibit near-infrared (NIR) absorptions (-1400 nm) based on an intramolecular charge-transfer interaction, changes in not only their structures but also their UV-vis-NIR spectra can be controlled by redox stimuli. In this Communication, we present an unprecedented one-step p-extension to pentacene from non-fused benzene rings by oxidation, and subsequent two-stage deannulation to benzene rings via anthracene upon reduction. All structures were determined by single-crystal X-ray analyses, and their properties were characterized by spectroscopic and theoretical studies.
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