Aggregation induced emissive carbazole-based push pull NLOphores: Synthesis, photophysical properties and DFT studies

被引:52
作者
Lanke, Sandip K. [1 ]
Sekar, Nagaiyan [1 ]
机构
[1] Inst Chem Technol, Dept Dyestuff Technol, Bombay 400019, Maharashtra, India
关键词
Aggregation induced emission; Photophysical properties; Twisted intramolecular charge transfer (TICT); Solvatochromism; Polarizability; Density functional theory (DFT); INTRAMOLECULAR CHARGE-TRANSFER; EXCITED-STATE; ENHANCED EMISSION; FLUORESCENT-PROBE; BIPOLAR HOST; DONOR; BLUE; DERIVATIVES; ABSORPTION; ACCEPTOR;
D O I
10.1016/j.dyepig.2015.09.013
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
2-Alkoxy-9-methyl-9H-carbazole-3-carbaldehyde based push pull chromophore were efficiently synthesized by a multi-step reaction starting from 9H-carbazole-2-ol. The fluorescence properties of these D-pi-A chromophores were investigated in various solvents of varying polarities and in mixed solvent solutions of DMF and H2O. They exhibited low fluorescent intensity in solution but a high fluorescent intensity in aggregate forms and in their solid state due to the promising aggregation-induced emission enhancement characteristics. These dyes were fully characterized by FT-IR, H-1 NMR and HRMS spectra. The ratio of ground to excited state dipole moment of the novel push pull chromophore were calculated by Bakhshiev and Bilot-Kawski correlations. All the four dyes show more or less twisted intramolecular charge transfer (TILT) characteristics. They show a large first hyperpolarizability value ranging from 189-721 x 10(-3) esu by theoretical method and 73-330 x 10(-30) esu by experimental method. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:82 / 92
页数:11
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