Hydrogen-bonding-aided synthesis of novel ladderlike organobridged polysiloxane containing side-chain naphthyl groups

With a hydrogen-bonding template, a novel soluble aryl amide-bridged ladderlike polysiloxane, containing naphthyl as the side-chain group, has been successfully synthesized via a stepwise coupling polymerization. It is proposed that the monomer,N,N'.-di(3-naphthyldiethoxylsilyl-propyl)-[4,4'-oxybis(benzyI amide)], prepared by Grignard and hydrosilylation reactions, undergoes self-assembly first via amido hydrogen bonding and then via hydrolysis, followed by condensation under controlled reaction conditions to yield a high molecular weight, soluble, dark yellow polymer. The analytical results (Fourier transform infrared, H-1 NMR, Si-29 NMR, X-ray diffraction, differential scanning calorimetry, and vapor pressure osmometry) show that the polymer possesses an ordered ladderlike architecture. (C) 2003 Wiley Periodicals, Inc.