Abstract
This article describes the syntheses and second-order nonlinear optical (NLO) properties of novel types of optically transparent polyamides containing second-order NLO-active chromophores with high density. The chromophore used in this study contained a perfluorooctylsulfonyl or cyano moiety as an electron-withdrawing group at the π-conjugating sites. The polyamides were prepared by condensation polymerization between 5-substituted isophthaloyl chloride derivatives and novel 3,5-diaminobenzoates. When the terminal groups in the side chain of each comonomer unit were different, amorphous polyamides exhibited good solubility in common organic solvents and provided optical-quality films by spin-coating. The optical transparency of the obtained polyamides was down to 400 nm. Second-harmonic generation (SHG) measurements of the obtained polyamides were carried out by the Maker fringe method using a Q-switched Nd:YAG laser as an exciting beam after corona-poling. One of the polyamides, which was prepared from 5-{2-[N-(4-cyanophenyl)-N-methylamino]ethoxy}isophthaloyl chloride and 2-{N-methyl-N-[4-(perfluorooctylsulfonyl)phenyl]amino}ethyl 3,5-diaminobenzoate, exhibited the desired optical-transparency and the second-order NLO coefficient, d33, of 4.4 ± 1.3 pm/V, retaining 94% of its original d33 after storage for 2 weeks at ambient temperature.
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