Hybrid materials covalently incorporated with isophorone-based dyes through sol-gel process for nonlinear optical applications.

Two new push-pull type second-order nonlinear optical (NLO) active isophorone-based alkoxysilane dyes with the same acceptor were synthesized and characterized. One silane (ICTES-HEMA) bears a chromophore with a hydroxyethyl methylamino donor and the other silane (ICTES-HMPP) is a bulkier analogue with a hydroxymethyl diphenylamino donor. Transparent, homogeneous films were prepared via the copolymerization of tetraalkoxysilane (TEOS) and different NLO silanes with the ratio of 5:1. The d(33) values obtained for the HEMA and HMPP films are 46.3 and 20.6 pm/V, respectively. Normalized UV-vis spectra reveal that the introduction of a diaryl group would help to prevent unfavorable organization of the chromophores. The reorientation dynamic stabilities of the samples were studied by second-harmonic generation (SHG) measurements, demonstrating that bulkier chromophores incorporated in sol-gel materials would not necessarily lead to higher stabilities over time.