Investigation of poly(arylenevinylene)s, 42. Synthesis of PPV-based copolymers containing alkyldiphenylamine and triphenylamine in the main chain

Abstract

PPV-based copolymers carrying in-chain tertiary amino groups have been synthesized by Horner-type polycondensation of arylamine dialdehydes and alkoxy-substituted xylylene bis(phosphonate)s: [-NR-C 6 H 4 -CH=CH-C 6 H 2 (OAlkyl) 2 -CH=CH-C 6 H 4 -] n 6. Several compounds with the general structure 6 and containing methylamino, cyclohexylamino, and phenylamino groups have been prepared and analyzed. Incorporation of electron-rich amino groups into the PPV backbone does not interrupt the main-chain conjugation but has the effect of reducing the oxidation potential, thus transforming these polymers into highly photoconducting and hole injecting/hole transporting materials. These new polymers were evaluated using photoluminescence and cyclic voltammetry methods and characterized by gel-permeation chromatography (GPC) and DSC. The chemical structure was confirmed by NMR- and UV/VIS absorption spectroscopy. The polymers 6 are well-defined, completely soluble materials of high molecular weight (M w > 20000). They possess all-trans vinylene units and exhibit a strong green photoluminescence (Φ PL 70%). Solution-cast solid films show an outstanding photoconductivity in the UV/VIS range.