Unprecedented intramolecular cyclization in strongly dipolar extended merocyanine dyes: A route to novel dyes with improved transparency, nonlinear optical properties and thermal stability

Parthasarathy, Venkatakrishnan and Castet, Frederic and Pandey, Ravindra and Mongin, Olivier and Das, Puspendu Kumar and Blanchard-Desce, Mierille (2016) Unprecedented intramolecular cyclization in strongly dipolar extended merocyanine dyes: A route to novel dyes with improved transparency, nonlinear optical properties and thermal stability. In: DYES AND PIGMENTS, 130 . pp. 70-78.

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Abstract

Novel magenta dyes were obtained via an unprecedented base-promoted intramolecular cyclization of strongly dipolar elongated merocyanine dyes bearing a phthalimide substituted tricyanopropylidene terminal segment. These shorter diarylpolyene derivatives retain a dipolar character and show a typical intramolecular charge transfer (ICT) transition. The cyclization noticeably modifies the electronic structure inducing both onset of bond length alternation and reduction of dipole moment as well as a marked hypsochromic and hypochromic shift of the ICT absorption band compared to their merocyanine precursors. Yet the new dyes show improved quadratic hyperpolarizability and thermal stability as compared to the merocyanine dyes having the same number of conjugated double bonds in the polyenic linker. As such these derivatives hold promise as new class of dyes for NLO materials and SHG probes. (C) 2016 Elsevier Ltd. All rights reserved.

Item Type:	Journal Article
Publication:	DYES AND PIGMENTS
Publisher:	ELSEVIER SCI LTD
Additional Information:	Copy right for this article belongs to the ELSEVIER SCI LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, OXON, ENGLAND
Keywords:	Merocyanine dyes; Hyperpolarizability; Hyper-Rayleigh scattering; Nonlinear optics; Intramolecular charge transfer
Department/Centre:	Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	19 Jul 2016 09:10
Last Modified:	19 Jul 2016 09:10
URI:	http://eprints.iisc.ac.in/id/eprint/54181

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