Facile access to conjugated polymers under aerobic conditions via Pd-Catalyzed direct arylation and aryl amination polycondensation

Water-Processable Self-Doped Conducting Polymers via Direct (Hetero)arylation Polymerization

“…Biphasic conditions also permit to eliminate the use of anhydrous solvents. In another publication, DHAP using refluxing dimethylformamide (DMF) under aerobic conditions has allowed the synthesis of polymers with good molecular weights . Nowadays, development of polymerization conditions tends to consider industrial and scale-up challenges, by trying to allow the presence of water and oxygen in the reactions.…”

Advances in applying C–H functionalization and naturally sourced building blocks in organic semiconductor synthesis

“…77,78 In recent years, Kanbara et al discovered that refluxing the solvent (toluene, o-xylene, or DMF) during the polymerization allows certain DArP reactions to proceed under aerobic conditions. 79,80 The aerobic DArP of 5-(2-ethylhexyl)thieno-[3,4-c]-pyrrole-4,6dione (TPD) with 2,7-dibromo-9,9-dioctylfluorene was accomplished in the refluxed toluene with a molecular weight up to 176.8 kg mol À1 . 79 In their other report, a copolymer of 3,4-ethylenedioxythiophene (EDOT) and 2,7-dibromo-9,9-dioctylfluorene with a molecular weight of 54.2 kg mol À1 was successfully synthesized via DArP under aerobic conditions by refluxing the solvent DMF.…”

“…79 In their other report, a copolymer of 3,4-ethylenedioxythiophene (EDOT) and 2,7-dibromo-9,9-dioctylfluorene with a molecular weight of 54.2 kg mol À1 was successfully synthesized via DArP under aerobic conditions by refluxing the solvent DMF. 80 The authors attributed this to efficient degassing of dissolved oxygen from the reaction mixture and prevention of resolubilizing oxygen. 79,80 Aside from DArP, the Kanbara group also reported a few oxidative C-H/C-H polymerizations carried out under aerobic conditions.…”

“…80 The authors attributed this to efficient degassing of dissolved oxygen from the reaction mixture and prevention of resolubilizing oxygen. 79,80 Aside from DArP, the Kanbara group also reported a few oxidative C-H/C-H polymerizations carried out under aerobic conditions. In the same paper where they achieved the initial oxidative C-H/C-H polymerization to synthesize D-A copolymers, they were able to conducted the same polymerization under aerobic atmosphere as well, obtaining a D-A copolymer with high molecular weight (23.2 kg mol À1 ) and only 2% homo-coupling defects.…”

An efficient Buchwald–Hartwig amination protocol enables the synthesis of new branched and polymeric hole transport materials for perovskite solar cells

“…Having assessed the robustness of the reaction conditions, we challenged them in a polymerization reaction. The literature reports very few examples of B-H polymerizations, [16][17][18][19] only in one case leading to a polymer (an aromatic amine-dialkylfluorene alternating copolymer) having applications in electronic devices. 16 We selected 2,7-dibromo-9-(1-octylnonyl)-9H-carbazole and 4-octyloxyaniline as the co-monomers according to both the similarity of the structure to the previously reported B-H polymer and to the superior performances as semiconductors in both OFETs and OPVs of polymers incorporating carbazole in the place of fluorene.…”