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

Abstract

Triphenylamine (TPA) based donor-acceptor-donor (D-A-D) compounds were synthesized that showed aggregation enhanced emission (AEE) and molecular conformation and packing dependent rare self-reversible thermofluorochromism in the solid state. 1, TPA substituted with phenylenediacetonitrile at both end displayed twisted molecular conformation whereas OCH3 substitution at ortho position of TPA (3-MTPA, 2) resulted in twisted conformation at one end and coplanar conformation at other end. 4-methoxytriphenylamine (4-MTPA) attached acceptor (3) displayed coplanar conformation on both end of the acceptor. Highly twisted conformation in 1 lead to strong fluorescence (16.8 %) and coplanar conformation in 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. Computational studies indicate that the molecular conformation and OCH3substitution influences on the HOMO-LUMO energy level of TPA derivatives.

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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, Accepted Manuscript
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    Self-reversible thermofluorochromism of D-A-D triphenylamine derivatives and effect of molecular conformation and packing

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

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