SYNTHESIS AND PROPERTIES OF HIGHLY SOLUBLE 3RD-ORDER OPTICALLY NONLINEAR CHROMOPHORES AND METHACRYLATE MONOMER BASED ON DISTYRYLBENZENE

A novel series of highly soluble distyrylbenzenes bearing poly(alkylen eoxy) and/or alkylsulfonyl solubilizing substituents has been synthesi zed using the stereoselective Wadsworth-Emmons reaction as a key step. The corresponding poly(alkyleneoxy) alkylsulfonyl 4,4'-disubstituted distyrylbenzene has been covalently incorporated into an acrylic monom er which has also been successfully co-polymerized with methyl methacr ylate (MMA). All the 4,4'-disubstituted distyrylbenzenes and the polya crylate based co-polymer show excellent solubility, processibility and thermal stability. Importantly, 2-(2-butoxyethoxy)ethoxy-hexylsulfony l 4,4'-disubstituted distyrylbenzene exhibits only a minor bathochromi c shift of the absorption maximum compared to those of the correspondi ng symmetrically 4,4'-disubstituted distyrylbenzenes; however, its thi rd-order optical nonlinearity derived from Z-scan measurements at 800 nm is approximately twice as large as those of its symmetrically 4,4'- disubstjtuted counterparts.