Issue 10, 2017

3-Piperazinyl propenylidene indolone merocyanines: consecutive three-component synthesis and electronic properties of solid-state luminophores with AIE properties

Abstract

A series of twelve 3-piperazinyl propenylidene indolone merocyanines was synthesized in a one-pot fashion using a consecutive three-component insertion-coupling-Michael addition sequence. Physical-organic treatment of the absorption data of a consanguineous series of this library allows semiquantitative Linear Free Energy Relationships (LFERs) to be established and confirmation of the positive absorption solvatochromicity. All Boc-substituted piperazinyl merocyanines display aggregation induced emission (AIE), which was corroborated for two solvent systems. In particular, crystallization-induced emission enhancement (CIEE) induced by ultrasonication could be shown for a model chromophore by confocal laser scanning microscopy (CLSM).

Graphical abstract: 3-Piperazinyl propenylidene indolone merocyanines: consecutive three-component synthesis and electronic properties of solid-state luminophores with AIE properties

Supplementary files

Article information

Article type
Research Article
Submitted
04 Mei 2017
Accepted
02 Jun. 2017
First published
08 Jun. 2017

Mater. Chem. Front., 2017,1, 2013-2026

3-Piperazinyl propenylidene indolone merocyanines: consecutive three-component synthesis and electronic properties of solid-state luminophores with AIE properties

M. Denißen, N. Nirmalananthan, T. Behnke, K. Hoffmann, U. Resch-Genger and T. J. J. Müller, Mater. Chem. Front., 2017, 1, 2013 DOI: 10.1039/C7QM00198C

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