Synthesis and fluorescence property of some novel 1,8-naphthalimide derivatives containing a thiophene ring at the C-4 position
Jin Zhengneng; Li Najun; Wang Chuanfeng; Jiang Huajiang; Lu Jianmei; Zhou Qizhong
| HERO ID | 3575652 |
|---|---|
| In Press | No |
| Year | 2013 |
| Title | Synthesis and fluorescence property of some novel 1,8-naphthalimide derivatives containing a thiophene ring at the C-4 position |
| Authors | Jin Zhengneng; Li Najun; Wang Chuanfeng; Jiang Huajiang; Lu Jianmei; Zhou Qizhong |
| Journal | Dyes and Pigments |
| Volume | 96 |
| Issue | 1 |
| Page Numbers | 204-210 |
| Abstract | 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 H-1 NMR, C-13 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 pi-pi 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. (C) 2012 Elsevier Ltd. All rights reserved. |
| Doi | 10.1016/j.dyepig.2012.07.018 |
| Wosid | WOS:000310409100028 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | Naphthalimide; Thiophene; Crystal structure; Pd-catalyzed direct C-H bond arylation; Fluorescence; Fluorescence lifetime |