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Synfacts 2009(3): 0273-0273  
DOI: 10.1055/s-0028-1087760
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Zwitterionic Picolinium Chromophores

Contributor(s): Timothy M. Swager, Trisha L. Andrew
Y. Xiong, H. Tang, J. Zhang, Z. Y. Wang*, J. Campo, W. Wenseleers, E. Goovaerts, W. Wang*
Carleton University, Ontario, Canada and University of Antwerp, Belgium
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Publication History

Publication Date:
19 February 2009 (online)

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Significance

A series of thermally-stable, ­zwitterionic chromophores (3a-d) were synthesized in one step with moderate yields. The synthesized dyes displayed large molecular hyper­polarizability (β) values (up to 1800 x 10-³0 esu) and could therefore be applied in an electro-optic device. Dyes 3a-d were found to form readily antiparallel H-aggregates due to their strong ground-state dipole moments. However, when dispersed in a polar polymer matrix, individual dye molecules could be isolated and poled in an electric field to yield acceptable electro-optic activity.