Several novel electro-optic (EO) D- p -A (EDG-[p-bridge]-EWG) chromophores based on the known Tolane template were synthesized using palladium coupling techniques between phenylacetylenes and aryl halides.  The molecules were selected under guidance by an inverse molecular design targeting visually transparent Donor-Acceptor chromophores with high EO activity. Two challenges arise in the design of transparent EO chromophores: 1) planarity of the bridging p-system, 2) non-symmetric substitution on the p-bridge.  A novel chromophore containing an intramolecular hydrogen bond was generated to enforce planarity of the p-bridge.  The synthetic difficulty revolved around the placement of hydrogen bonding groups which needed to be installed without a large tradeoff involving D- p -A electronic effects.  To address the second challenge, a class of compounds with varying naphthalene and anthracene p-bridges was also synthesized to generate novel non-symmetric chromophores from a precursor class of symmetric chromophores.

Synthesis of novel transparent electro-optic chromophores

243rd National Meeting (2012)

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