Diindeno-Fused Corannulene-Extended Tetrathiafulvalenes

IF 3 4区 化学 Q3 CHEMISTRY, PHYSICAL ChemPhotoChem Pub Date : 2024-06-04 DOI:10.1002/cptc.202400122
Dr. Viktor Bliksted Roug Pedersen, Prof. Dr. Ramesh Jasti, Prof. Dr. Mogens Brøndsted Nielsen
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Abstract

Two regioisomeric extended tetrathiafulvalenes (TTFs) incorporating diindeno-fused corannulene spacers were synthesized from suitable dione precursors using Horner-Wadsworth-Emmons olefination reactions. Both compounds are strong chromophores with a longest-wavelength absorption that exhibited some degree of charge-transfer character as inferred from solvatochromic behaviors and frontier orbital calculations. The compounds underwent two reversible one-electron oxidations and a quasi-reversible third oxidation during cyclic voltammetry conditions. The mono- and dications had characteristic NIR absorptions and both were EPR active. The dications with potential diradicaloid characters underwent reactions when generated in bulk.

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二茚并入芫荽烯-扩展四硫杂戊烯
利用 Horner-Wadsworth-Emmons 烯化反应,从合适的二酮前体合成了两种含有二茚并熔茱萸烯间隔物的广义四硫杂戊烯(TTF)。根据溶解变色行为和前沿轨道计算推断,这两种化合物都是具有最长吸收波长的强发色团,并表现出一定程度的电荷转移特性。在循环伏安条件下,这些化合物经历了两次可逆的单电子氧化和准可逆的第三次氧化。单阳离子和双阳离子具有特征性的近红外吸收,并且都具有 EPR 活性。具有潜在类二极体特征的二阳离子在批量生成时发生了反应。
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来源期刊
ChemPhotoChem
ChemPhotoChem Chemistry-Physical and Theoretical Chemistry
CiteScore
5.80
自引率
5.40%
发文量
165
期刊介绍: Light plays a crucial role in natural processes and leads to exciting phenomena in molecules and materials. ChemPhotoChem welcomes exceptional international research in the entire scope of pure and applied photochemistry, photobiology, and photophysics. Our thorough editorial practices aid us in publishing authoritative research fast. We support the photochemistry community to be a leading light in science. We understand the huge pressures the scientific community is facing every day and we want to support you. Chemistry Europe is an association of 16 chemical societies from 15 European countries. Run by chemists, for chemists—we evaluate, publish, disseminate, and amplify the scientific excellence of chemistry researchers from around the globe.
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