Synthesis and Electronic, Photophysical, and Electrochemical Properties of a Series of Thienylcarbazoles

详细信息    查看全文

• 作者：Shin-ichiro Kato ; Satoru Shimizu ; Hiroaki Taguchi ; Atsushi Kobayashi ; Seiji Tobita ; Yosuke Nakamura
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：April 6, 2012
• 年：2012
• 卷：77
• 期：7
• 页码：3222-3232
• 全文大小：556K
• 年卷期：v.77,no.7(April 6, 2012)
• ISSN：1520-6904

文摘

A series of thienylcarbazoles were synthesized by Suzuki鈥揗iyaura and Ullmann coupling reactions. In these compounds, the 2-thienyl or 2,2鈥?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鈥搗is 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 蟺-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 蟺-conjugation, the resulting HOMO鈥揕UMO gaps, and fluorescence efficiency. The crystal structures of 5 and 9 were also disclosed.