Premium
Investigation of poly(arylenevinylene)s, 42. Synthesis of PPV‐based copolymers containing alkyldiphenylamine and triphenylamine in the main chain
Author(s) -
Pfeiffer Steffen,
Rost Henning,
Hörhold HansHeinrich
Publication year - 1999
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/(sici)1521-3935(19991101)200:11<2471::aid-macp2471>3.0.co;2-0
Subject(s) - triphenylamine , copolymer , polymer chemistry , gel permeation chromatography , alkoxy group , photoluminescence , condensation polymer , polymer , side chain , materials science , cyclic voltammetry , chemistry , organic chemistry , alkyl , electrochemistry , optoelectronics , electrode
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 > 20 000). 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.