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Self-reversible thermofluorochromism of D–A–D triphenylamine derivatives and the effect of molecular conformation and packing

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Abstract

Triphenylamine (TPA) based donor–acceptor–donor (D–A–D) compounds were synthesized showing aggregation enhanced emission (AEE) and molecular conformation and packing dependent rare self-reversible thermofluorochromism in the solid state. 1, with TPA substituted with phenylenediacetonitrile at both ends, displayed a twisted molecular conformation, whereas OCH3 substitution at the ortho position of TPA (3-MTPA, 2) resulted in a twisted conformation at one end and a coplanar conformation at the other end. The 4-methoxytriphenylamine (4-MTPA) substituted acceptor (3) displayed a coplanar conformation at both ends of the acceptor. The highly twisted conformation of 1 led to strong fluorescence (16.8%) and the coplanar conformation of 3 resulted in weak fluorescence (1.6%) in the solid state. 2 showed moderate fluorescence (8.4%) in the solid state. Importantly, 1 and 2 exhibited self-reversible thermofluorochromism with heating and cooling, whereas 3 did not show any fluorescence switching with temperature change. Computational studies indicate that the molecular conformation and OCH3 substitution influence the HOMO–LUMO energy level of TPA derivatives.

Graphical abstract: Self-reversible thermofluorochromism of D–A–D triphenylamine derivatives and the effect of molecular conformation and packing

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Publication details

The article was received on 24 Aug 2017, accepted on 08 Oct 2017 and first published on 09 Oct 2017


Article type: Paper
DOI: 10.1039/C7CE01538K
Citation: CrystEngComm, 2017, Advance Article
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    Self-reversible thermofluorochromism of D–A–D triphenylamine derivatives and the effect of molecular conformation and packing

    A. Kundu, S. Karthikeyan, D. Moon and S. P. Anthony, CrystEngComm, 2017, Advance Article , DOI: 10.1039/C7CE01538K

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