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Accessing New DPP‐Based Copolymers by Direct Heteroarylation Polymerization
Author(s) -
Pouliot JeanRémi,
Mercier Lauren G.,
Caron Samuel,
Leclerc Mario
Publication year - 2013
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.201200573
Subject(s) - copolymer , polymerization , pyrrole , polymer chemistry , materials science , band gap , density functional theory , derivative (finance) , chemistry , computational chemistry , polymer , organic chemistry , optoelectronics , financial economics , economics , composite material
A diketopyrrolopyrrole derivative was copolymerized with different electron‐withdrawing units [i.e., thieno[3,4‐ c ]pyrrole‐4,6‐dione ( TPD ), bis(thieno[3,4‐ c ]pyrrole‐4,6‐dione) ( BTPD ), and 3,4‐dicyanothiophene ( DCT )] using direct heteroarylation polymerization (DHAP) methodology. Alternating copolymers with low‐lying frontier orbitals suitable for n‐type semiconducting behavior were obtained. Under optimized conditions, polymerization reactions were reproducible and high number‐average molecular weights ( M n ) were achieved. Density functional theory (DFT) calculations indicated that the structures with the lowest conformational energy had planar backbones. Preliminary results showed that these new low‐bandgap materials exhibit good n‐type behavior.