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Unprecedented intramolecular cyclization in strongly dipolar extended merocyanine dyes: A route to novel dyes with improved transparency, nonlinear optical properties and thermal stability
Published in Elsevier Ltd
2016
Volume: 130
   
Pages: 70 - 78
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. © 2016 Elsevier Ltd.
About the journal
JournalData powered by TypesetDyes and Pigments
PublisherData powered by TypesetElsevier Ltd
ISSN01437208
Open AccessYes
Concepts (16)
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    Bond length
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    Charge transfer
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    Cyclization
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    Electronic structure
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    Optical properties
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    Organic polymers
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    Thermodynamic stability
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    BOND LENGTH ALTERNATION
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    HYPER RAYLEIGH SCATTERING
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    Hyper-polarizability
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    Intra-molecular charge transfer
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    Intramolecular charge transfers
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    INTRAMOLECULAR CYCLIZATIONS
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    MEROCYANINE DYE
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    Non-linear optical properties
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    Nonlinear optics