Student Project Abstracts 2005 - Pluto - University of Washington

Synthesis and Characterization of Extended Squaraine CompoundsTehetena MesganawGeorgia Institute of TechnologyShijun Zheng and Seth MarderMarder Lab, School of Chemistry and BiochemistryGeorgia Institute of TechnologyINTRODUCTIONOrganic dyes encompass a broad range of applications thatare being investigated in the quest for new advancements in varioustechnological areas. Squaraines are a novel class of organicdyes that have delocalized π-electron systems that absorb at long(near infrared) wavelengths. These extended squaraines with alkylside chains can easily form good optical quality, thin films.These molecules are nonlinear optical materials and as such canpotentially be used for optical switching applications. In a nonlinearoptical material, when the light intensity shined on the materialincreases, the electron cloud distorts, and the refractive indexchanges. As a result, the way light propagates through the materialchanges. Therefore, squaraine compounds are on the rise anddemands for these dyes will increase rapidly in years to come.RESEARCH METHODSynthesis of (1)The synthesis of (1) provides one of the building blocks forthe final squaraine compound. Excess pyrrole was reacted with11-bromomethyl-tricosane in the presence of NaH and DMF. Thereaction was done under N 2at 60 ºC and left for 3 days. The desiredproduct (1) resulted in a yield of