Synthesis and fluorescence property of some novel 1,8-naphthalimide derivatives containing a thiophene ring at the C-4 position

详细信息    查看全文

• 作者：Jin Zhengneng ; Li Najun ; Wang Chuanfeng ; Jiang Huajiang ; Lu Jianmei ; Zhou Qizhong
• 关键词：Naphthalimide ; Thiophene ; Crystal structure ; Pd-catalyzed direct C&ndash ; H bond arylation ; Fluorescence ; Fluorescence lifetime
• 刊名：Dyes and Pigments
• 出版年：2013
• 出版时间：January, 2013
• 年：2013
• 卷：96
• 期：1
• 页码：204-210
• 全文大小：1088 K

文摘

A series of novel 1,8-naphthlimide derivatives containing a thiophene ring at the C-4 position was synthesized through Pd-catalyzed direct C-H bond arylation and characterized by ¹H NMR, ¹³C NMR, MALDI-HRMS and elemental analysis. The crystal structure of N-hexyl-4-(benzo[b]thiophen-2-yl)-1,8-naphthalimide was found to be a kite structure. The moderate ¦Ð-¦Ð stacking interaction between the two core planes (naphthalimide ring) and the van der Waals' forces between the flexible hexyl groups constructed a 3D structure. The UV-vis and fluorescence property of synthesized compounds in chloroform were investigated. All compounds can emit blue, green or yellow emission except for N-hexyl-4-(5-nitrothiophene-2-yl)-1,8-naphthalimide. The results show that the 1,8-naphthalimide derivatives with an electron-donating group on the thiophene ring or larger conjugated structure have enhanced fluorescence properties.