Synthesis and Electronic, Photophysical, and Electrochemical Properties of a Series of Thienylcarbazoles
Synthesis and Electronic, Photophysical, and Electrochemical Properties of a Series of Thienylcarbazoles
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DOI：
10.1021/jo202625p
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发表时间：
2012-04-06
影响因子：
3.6
通讯作者：
Nakamura, Yosuke
中科院分区：
文献类型：
--
作者：
Kato, Shin-ichiro;Shimizu, Satoru;Nakamura, Yosuke
通过Suzuki-Miyaura偶联反应和Ullmann偶联反应合成了一系列噻吩基咔唑。在这些化合物中，2-噻吩基或2，2 ′-联噻吩-5-基在咔唑环的N-、1，8-、3，6-、2，7-、2，7，N-或1，8，N-位连接。通过紫外可见光谱、荧光光谱、循环伏安法（CV）和密度泛函理论（DFT）计算，探讨了结构变化对它们的电子、物理和电化学性质的影响。在4、5和10中的2，7-位处的噻吩基取代基负责高程度的π-共轭和具有高达0.61的荧光量子产率的强发射。对一系列噻吩基咔唑的CV研究表明，3，6-取代咔唑3和9具有良好的给电子能力。噻吩单元的数目被发现影响π-共轭的程度，所得到的HOMO-LUMO间隙，和荧光效率。并对化合物5和9的晶体结构进行了表征。
A series of thienylcarbazoles were synthesized by Suzuki-Miyaura and Ullmann coupling reactions. In these compounds, the 2-thienyl or 2,2'-bithiophen-5-yl group is connected at the N-, 1,8-, 3,6-, 2,7-, 2,7,N-, or 1,8,N-positions of the carbazole ring. The effects of structural variations on their electronic, photophysical, and electrochemical properties were explored by UV-vis and fluorescence spectroscopies, cyclic voltammetry (CV), and DFT calculations in evaluation of their potential as material components. The thienyl substituents at the 2,7-positions in 4, 5, and 10 are responsible for a high degree of pi-conjugation and strong emission with fluorescence quantum yields up to 0.61. The CV on a series of thienylcarbazoles revealed a good electron-donating ability of 3,6-substituted carbazoles 3 and 9. The number of thiophene units was found to affect the extent of pi-conjugation, the resulting HOMO-LUMO gaps, and fluorescence efficiency. The crystal structures of 5 and 9 were also disclosed.