A new traceless aniline linker was developed to synthesize the azomethines, benzoxazoles, benzothiazoles and benzimidazoles on a solid support. The loading of the substrates on the solid support and the cleavage from the solid support were performed by an imine synthesis and by imine-exchanged process under the mild conditions, respectively. Utilizing the linker we have prepared 28 azomethine compounds as candidates for new liquid crystals though three-step combinatorial solid-phase parallel synthesis. Products with a thioester group exhibited liquid crystalline properties with the higher transition temperatures than the others. 6 Kinds of benzoxazoles, benzothiazoles and benzimidazoles have been also synthesized by imine-exchange reaction with concomitant air oxidation of the substates.
