Balanced Ambipolar Poly(diketopyrrolopyrrole‐alt‐tetrafluorobenzene) Semiconducting Polymers Synthesized via Direct Arylation Polymerization

Abstract

The synthesis of an ambipolar π-conjugated copolymer consisting of alternating diketopyrrolopyrrole and tetrafluorobenzene via direct arylation polymerization (DAP) is reported. Two different combinations of monomers are investigated under various catalytic conditions for DAP. The target polymer obtained under an optimized catalytic condition shows minimal structural defects, a number-average molecular weight of 33.2 kDa, and balanced electron and hole mobility of 1 × 10(-2) cm(2) V(-1) S(-1) in the organic field-effect transistors fabricated and tested under ambient conditions.

Analysis of diverse direct arylation polymerization (DArP) conditions toward the efficient synthesis of polymers converging with stille polymers in organic solar cells

“…Of particular importance in DArP is the influence of functionality on synthetic performance. Recently, our group and Wang et al made critical observations about which coupling partner should be halogenated for optimal DArP performance with highly fluorinated substrates. Though the system presented here is very different because only thiophene has sufficiently acidic protons, it is worth noting that given these two substrates (phenylene and BT), there are two routes that can be used to generate the same polymer.…”

CH Activation as a Shortcut to Conjugated Polymer Synthesis

“…This risk is absent when the brominated monomer in a copolymerization is either a C 6 arene or a thiophene structure which does not have available CH bonds adjacent to the CBr bond . This may explain the high quality of polymers obtained in these instances …”

Direct arylation polymerization toward efficient synthesis of benzo[1,2‐c:4,5‐c'] dithiophene‐4,8‐dione based donor‐acceptor alternating copolymers for organic optoelectronic applications

“…We carried out a preliminary optimization for the direct arylation of BDTD with CH active donors by testing two direct arylation conditions using Pd 2 (dba) 3 and Hermann's catalyst, respectively, in the synthesis of P1 and P2 (Table ). Both these conditions have been previously optimized for the C‐H activation of thiophene‐flanked monomers and have been used for synthesizing a variety of linear and 2D/3D conjugated networks. P1 was obtained in relatively low yields from both conditions since majority of products were obtained as oligomers in the hexane fraction (Supporting Information Fig.…”