Tetrathienyl Corannulene Compounds with Highly Sensitive Photochromism
Tetrathienyl Corannulene Compounds with Highly Sensitive Photochromism
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具有高灵敏光致变色性的四噻吩基Corannulene化合物
DOI：
10.1002/chem.202201286
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发表时间：
2022
期刊：
影响因子：
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通讯作者：
Kawai Tsuyoshi
中科院分区：
文献类型：
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作者：
Yamada Mihoko;Sawazaki Tomoya;Fujita Mae;Asanoma Fumio;Nishikawa Yoshiko;Kawai Tsuyoshi
我们设计并合成了光致变色四噻吩基环烯化合物1,2,7,8 -四基（2 -甲基- 5 -苯基噻吩- 3 -基）环烯(1)和1,2,7,8 -四基（2,4 -二甲基- 5 -苯基噻吩- 3 -基）环烯(2)，通过将两个单位的光致变色环氧乙烯与具有良好天线效应的弯曲芳香环烯融合。化合物1表现出高度敏感的光反应性，具有8.2×104M−1cm−1的大摩尔吸收系数和几乎光子定量的光循环。另一方面，具有平面芳香菲的terarlene衍生物9,10‐双（2,4‐二甲基‐5‐苯基噻吩‐3‐基）菲(4)没有光反应性。造成这种差异的原因是由于能量迁移放大的光反应性旋回体占主导地位，以及弯曲结构导致的活性碳之间的距离缩短。
We have designed and synthesized photochromic tetrathienyl corannulene compounds, 1,2,7,8‐tetrakis(2‐methyl‐5‐phenylthiophen‐3‐yl)corannulene (1) and 1,2,7,8‐tetrakis(2,4‐dimethyl‐5‐phenylthiophen‐3‐yl)corannulene (2), by fusing two units of photochromic terarylene with a curved aromatic corannulene with a promising antenna effect. Compound1exhibited highly sensitive photoreactivity, with a large molar absorption coefficient of 8.2×104M−1cm−1and practically photon‐quantitative photocyclization. On the other hand, a terarylene derivative with a planar aromatic phenanthrene, 9,10‐bis(2,4‐dimethyl‐5‐phenylthiophen‐3‐yl)phenanthrene (4) showed no photoreactivity. The reason for such a difference was attributed to the predominance of the photoreactive atropisomers amplified by energy migration, and the shortened distance between reactive carbons induced by the curved structure.