Issue 25, 2019, Issue in Progress

The enhancement of the D–A effect of an asymmetric Schiff base by introducing acetyl groups into diaminomaleonitrile: synthesis, red fluorescence and crystal structure

Abstract

An asymmetrical salen-type organic ligand was designed and synthesized by a new strategy developed using a precursor Ac-DMN, which is a diaminomaleonitrile (DMN) incorporated with an acetyl group. In this study, two types of asymmetrical ligands, namely Ac-DMN-salicylaldehyde (L0) and Ac-DMN-4-N,N-diethyl-salicylaldehyde (L1), and their Zn(II) coordination complexes were studied. With the electron-pushing substituent, L1 showed interesting photoluminescence behaviour distinct from that of L0. In a THF solution, the maximum fluorescence emission of L1 red-shifted to 90 nm compared with that of L0. Furthermore, in a THF–H2O solution, L1 exhibited aggregation-induced emission (AIE), but L0 exhibited aggregation-caused quenching (ACQ). Upon coordination with Zn(II), the maximum emission wavelengths in THF for both the ligands were red-shifted to 100 nm and 105 nm, respectively. The crystalline solid-state photoluminescence properties were studied based on the single-crystal structural analysis.

Graphical abstract: The enhancement of the D–A effect of an asymmetric Schiff base by introducing acetyl groups into diaminomaleonitrile: synthesis, red fluorescence and crystal structure

Supplementary files

Article information

Article type
Paper
Submitted
05 Feb 2019
Accepted
23 Apr 2019
First published
08 May 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 14268-14275

The enhancement of the D–A effect of an asymmetric Schiff base by introducing acetyl groups into diaminomaleonitrile: synthesis, red fluorescence and crystal structure

K. Wang, H. Su, P. Wang, W. Wang and H. Li, RSC Adv., 2019, 9, 14268 DOI: 10.1039/C9RA00977A

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