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TitleSynthesis and solution aggregation studies of a suite of mixed neutral and zwitterionic chromophores for second-order nonlinear optics
Publication TypeJournal Article
Year of Publication2014
AuthorsPeddie, V., Anderson J., Harvey J.E., Smith G.J., and Kay A.
JournalJournal of Organic Chemistry
Pagination10153 - 10169
Date Published2014
ISSN00223263 (ISSN)
Keywordsampholyte, aniline, article, chromatophore, Chromophores, dipole, Electrostatic effect, Grignard reaction, Ground state, Hyper-polarizability, Intramolecular interactions, Neutral ground state, Nonlinear optics, nonlinear system, Optical nonlinearity, Optics, Organic materials, Polymerization, Second order nonlinear optics, solvent, Solvents, Strong dependences, synthesis
AbstractWe report details of the synthesis of a series of bi- and trichromophores. These compounds contain mixtures of chromophores that have zwitterionic (ZWI) and neutral ground state (NGS) components covalently attached to each other. The neutral ground state moieties are based on dyes with aniline donors - such as Disperse Red 1 - whereas the zwitterionic components are derived from chromophores with pro-aromatic donors such as 1,4-dihydropyridinylidene. By combining both ZWI and NGS components, we aim to develop novel compounds for nonlinear optics in which there is an enhancement of the overall hyperpolarizability coupled with a decrease in the net dipole moment. Thus, this approach should eliminate the electrostatic effects that result when only one type of chromophore is used, and so reduce the likelihood of undesirable aggregation occurring. This, in turn, should enable us to realize organic materials with large macroscopic optical nonlinearities. An analysis of the UV-vis results suggests that there is a strong dependence on solvent polarity that determines whether the embedded constituents should be treated as discrete elements; in low polarity solvents, there appear to be strong intramolecular interactions occurring, particularly when a 1,4-quinolinylidene-based donor is used in the ZWI component. © 2014 American Chemical Society.

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