MODIFIED HORNER-EMMONS REACTION OF POLYMERIC PHOSPHONATES - VERSATILESYNTHESIS OF PENDANT STILBENE-CONTAINING POLYMERS

Poly[styrene-co-(diethyl vinylbenzylphosphonate)] and poly[methylmetha crylate-co-(diethyl vinylbenzylphosphonate)] were prepared and used in modified Horner-Emmons reactions to synthesize polymers with covalent ly attached stilbene groups. This versatile new method allowed for the preparation of polymers with either electron-donor (OCH3, CH3) or ele ctron-acceptor (Br, NO2) substituents on the stilbene aromatic ring. T he resulting polymers were characterized by H-1 NMR, FT-IR, UV-visible , DSC, and size exclusion chromatography. Efficient transformation of polymeric phosphonates to the polymeric stilbene derivatives was reali zed. Size exclusion chromatographic analyses demonstrated that the rea ction conditions have no deleterious effect on the molecular weight di stribution of the various polymers that were prepared. Photochromic be havior was demonstrated for one of the derivatives. (C) 1995 John Wile y and Sons, Inc.