Self-organized one-dimensional columns of benzo[b]thiophene-fused tetraazaporphyrins

Abstract

Ring-expanded metallophthalocyanines fused with thiophene rings 1–4 have been synthesized by ring closing reaction from the o-chloroethynylbenzene substructures with Na 2 S 9 H 2 O . The self-organizing properties of these compounds have been studied by UV-vis spectroscopy in solution, π-A isotherms at air-water interface, X-ray diffraction (XRD) patterns of a solid, and atomic force microscopy (AFM). Whereas all compounds exhibit good solubility in organic solvents, thiophene-fused phthalocyanines form stable aggregates through strong intermolecular π–π interaction. Copper phthalocynaine Cu -2 possessing phenyl spacers produced long nano-fibrous assemblies from solution.