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Red Emitting Diphenylpyrrolopyrrole (DPP)‐Based Polymers Prepared by Stille and Heck Coupling
Author(s) -
Zhu Yu,
Heim Ingo,
Tieke Bernd
Publication year - 2006
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/macp.200600363
Subject(s) - stille reaction , thiophene , polymer , conjugated system , polymer chemistry , pyrrole , condensation polymer , heck reaction , chemistry , photoluminescence , alkyl , materials science , photochemistry , organic chemistry , aryl , optoelectronics
Abstract Summary: Six new soluble conjugated polymers are described, which were prepared by Stille and Heck polycondensation reactions. They alternately consist of dialkylated 1,4‐diketo‐3,6‐diphenyl‐pyrrolo[3,4‐c]pyrrole (DPP) units and divinylbenzene or thiophene‐based units. The polymers were prepared from 1,4‐diketo‐2,5‐dialkyl‐3,6‐di(4‐bromophenyl)‐pyrrolo[3,4‐c]pyrrole with alkyl being hexyl ( 1a ), methyl ( 1b ), and 2‐ethylhexyl ( 1c ) and 2,5‐bis(tributylstannyl)thiophene ( 2 ), 5,5′‐bis(tributylstannyl)bithiophene ( 3 ), 3,4‐ethylenedioxythiophene ( 4 ) and divinylbenzene ( 5 ). The new polymers exhibit brilliant red purple color and strong photoluminescence in common organic solvents. The DPP‐phenylenevinylene copolymers exhibit molecular weights up to 41 000 Da, and the poly(DPP‐thienylene)s up to 12 200 Da. In chloroform, the poly(DPP‐thienylene)s exhibit absorption and photoluminescence maxima up to 560 and 624 nm, respectively, the corresponding maxima of the poly(DPP‐phenylenevinylene)s are at 529 and 640 nm, respectively. Quantum yields of fluorescence up to 36% were determined. Cyclic voltammetric studies indicate quasi‐reversible oxidation ( p ‐doping) of the poly(DPP‐thienylene)s and irreversible reduction ( n ‐doping) of all polymers.Molecular structure of polymers.