ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis and properties of butterfly-shaped naphthalimide-based AIE-active fluorescent dyes

Hui Zhang, Meng Zhou, Haina Wang, Yuling Zhao, and Tianzhi Yu

Key Laboratory of Opto-Electronic Technology and Intelligent Control (Ministry of Education), Lanzhou Jiaotong University, Lanzhou, China

E-mail: yutzh@mail.lzjtu.cn

Received: 15 June 2021  Accepted: 29 December 2021

Abstract:

Two novel butterfly-shaped naphthalimide derivatives, 1,3-bis((carbazole-9-yl)-4-benzene-4–1,8-naphthalimide-N-)2,4,6-trimethylbenzene (DNI-Cz) and 1,3-bis((4-triphenylamine)-4–1,8-naphthalimide-N-)2,4,6-trimethylbenzene (DNI-TPA), were designed and synthesized. The D-π-A-π-D-type molecules exhibit typical aggregation-induced emission (AIE) effects. The fluorescence intensities of the two derivatives were weak in pure DMF but sharply increased to 89-fold and 171-fold, while the water content increased to 70% and 80% in the mixed DMF/H₂O. The photophysical properties, electrochemical properties, thermal stabilities, fluorescence lifetime and yield were studied. The two derivatives showed long fluorescence lifetimes with respective 8.63 ns and 16.32 ns and fluorescence quantum yields of 81.32% and 79.09%. In addition, due to the good thermal stability and luminescent properties, DNI-Cz and DNI-TPA are ideal candidates for promising applications in organic light-emitting diodes (OLEDs).

Keywords: Naphthalimide; Carbazole; Triphenylamine; AIE; D-π-A-π-D

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-021-02058-z

Chemical Papers 76 (4) 2397–2404 (2022)