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

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 semiquantita...

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Published in:Materials chemistry frontiers 2017-10, Vol.1 (10), p.2013-2026
Main Authors: Denißen, Melanie, Nirmalananthan, Nithiya, Behnke, Thomas, Hoffmann, Katrin, Resch-Genger, Ute, Müller, Thomas J. J.
Format: Article
Language:English
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Summary: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).
ISSN:2052-1537
2052-1537
DOI:10.1039/C7QM00198C