title: Simple synthesis of P(Cbz-alt-TBT) and PCDTBT by combining direct arylation with suzuki polycondensation of heteroaryl chlorides.
abstract: Direct arylation (DA) of 2-chlorothiophene and 2-chloro-3-hexylthiophene with 4,7-dibromo-2,1,3-benzothiadiazole is used to synthesize 4,7-bis(5-chloro-2-thienyl)-2,1,3-benzothiadiazole (TBTCl2) and 4,7-bis(5-chloro-4-hexyl-2-thienyl)-2,1,3-benzothiadiazole (DH-TBTCl2) in one step. Suitable conditions of the Suzuki polycondensations (SPC) of TBTCl2 and DH-TBTCl2 with the carbazole comonomer CbzPBE2 are established, furnishing PCDTBT and P(Cbz-alt-TBT) with high molecular weight and yield. Compared with control samples made from the corresponding dibromides, high-temperature NMR and UV-vis spectroscopy indicate similar properties for PCDTBT but an increased content of Cbz-Cbz homocouplings for P(Cbz-alt-TBT).
authors.affiliation: Makromolekulare Chemie, Universität Freiburg, Stefan-Meier-Straße 31, 79104, Freiburg, Germany; Optoelectronics Group, Cavendish Laboratory, J J Thomson Avenue, Cambridge, CB3 0HE, UK.
authors.forename: Florian
authors.initials: F
authors.lastname: Lombeck
authors.forename: Rukiya
authors.initials: R
authors.lastname: Matsidik
authors.forename: Hartmut
authors.initials: H
authors.lastname: Komber
authors.forename: Michael
authors.initials: M
authors.lastname: Sommer
mesh_terms: D002227:Carbazoles / Q000737:chemistry; D002712:Chlorides / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D058105:Polymerization; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry; D013053:Spectrophotometry; D013830:Thiadiazoles / Q000138:chemical synthesis / Q000737:chemistry*; D013876:Thiophenes / Q000737:chemistry
chemical_list: D002227:Carbazoles; D002712:Chlorides; D006841:Hydrocarbons, Aromatic; D011108:Polymers; D013830:Thiadiazoles; D013876:Thiophenes; C041514:carbazole; C015700:benzo-1,2,3-thiadiazole
keywords: Suzuki polycondensation; conjugated polymers; direct arylation; heteroaryl chlorides; homocoupling