title: Polymerization of tellurophene derivatives by microwave-assisted palladium-catalyzed ipso-arylative polymerization.
abstract: We report the synthesis of a tellurophene-containing low-bandgap polymer, PDPPTe2T, by microwave-assisted palladium-catalyzed ipso-arylative polymerization of 2,5-bis[(α-hydroxy-α,α-diphenyl)methyl]tellurophene with a diketopyrrolopyrrole (DPP) monomer. Compared with the corresponding thiophene analog, PDPPTe2T absorbs light of longer wavelengths and has a smaller bandgap. Bulk heterojunction solar cells prepared from PDPPTe2T and PC71 BM show PCE values of up to 4.4%. External quantum efficiency measurements show that PDPPTe2T produces photocurrent at wavelengths up to 1 µm. DFT calculations suggest that the atomic substitution from sulfur to tellurium increases electronic coupling to decrease the length of the carbon-carbon bonds between the tellurophene and thiophene rings, which results in the red-shift in absorption upon substitution of tellurium for sulfur.
authors.affiliation: Center for Functional Nanomaterials, Brookhaven National Laboratory, Upton, NY 11973 (USA).
authors.forename: Young S
authors.initials: YS
authors.lastname: Park
authors.forename: Qin
authors.initials: Q
authors.lastname: Wu
authors.forename: Chang-Yong
authors.initials: CY
authors.lastname: Nam
authors.forename: Robert B
authors.initials: RB
authors.lastname: Grubbs
mesh_terms: D002384:Catalysis; D008872:Microwaves; D008958:Models, Molecular; D016566:Organoselenium Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D058105:Polymerization; D011758:Pyrroles / Q000737:chemistry; D012993:Solar Energy; D013691:Tellurium / Q000737:chemistry*; D013876:Thiophenes / Q000737:chemistry*
chemical_list: D016566:Organoselenium Compounds; D011758:Pyrroles; D013876:Thiophenes; D010165:Palladium; D013691:Tellurium
keywords: ipso-arylative polymerization; low-bandgap polymers; microwave-assisted reactions; organic solar cells; tellurophene