A systematic study of the reaction of 1-chloromethyl-4-(2-trichlorosil
ylethyl)-benzene (coupling agent) with the surface Si-OH groups of gla
ss for times from 15 min to 48 h, followed by stilbazole chromophore p
recursor deposition/quaternization, is reported. Second harmonic gener
ation characteristics of these thin film materials indicate that a 15
min coupling agent reaction attains approximately 65% of full surface
coverage (based on chi(zzz)(2)) of benzylic chloride moieties, but tha
t 24 h is the optimal time for maximum coverage. The surface-anchored
chromophoric chloride salts in such materials undergo facile ion excha
nge with iodide, p-aminobenzenesulphonate, and ethyl orange, leading t
o enhancements in chi(zzz)(2) of up to 50%.