Direct Heteroarylation versus Stille Polycondensation Reaction for the Synthesis of TQ1 Conjugated Polymer

Abstract

We report a facile synthesis of the well‐known and highly promising conjugated polymer TQ1 using eco‐friendly direct heteroarylation reaction. Optimization of the reaction conditions yielded the target polymer with good optoelectronic and charge‐transport characteristics. The TQ1 polymer obtained in the direct heteroarylation reaction delivered power conversion efficiency of ∼5% in organic bulk heterojunction solar cells, which matches well the characteristics of the reference devices assembled using TQ1 batch synthesized via conventional Stille polycondensation reaction. The obtained results highlight the potential of the direct heteroarylation reaction as an efficient and environment‐friendly alternative to Stille cross‐coupling in the design of high‐quality semiconductor materials for organic electronics. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 776–782

Stille polycondensation: a multifaceted approach towards the synthesis of polymers with semiconducting properties

“…An increasing number of studies have compared the optical and electronic properties of polymers made using the DARP method versus those made using the Stille reaction, and have shown that similar properties can be achieved. 122,[125][126][127][128][129][130] In this article, we will delve into a comprehensive comparison between the Stille reaction and the DARP method.…”

Direct (Hetero)arylation: A Tool for Low-Cost and Eco-Friendly Organic Photovoltaics

“…Furthermore, Troshin et al 79 reported the synthesis of the low-cost material TQ1 (see Figure 2) by DHAP and compared its properties with the Stille-based polymer. After careful reaction optimizations, the authors were able to obtain a M n of about 30−33 kg mol −1 for both DHAP and Stille reactions.…”

Real-time monitoring polymerization degree of organic photovoltaic materials toward no batch-to-batch variations in device performance

“… 1 , 2 , 12 , 14 – 19 ) are ubiquitous in all kinds of synthetic conjugated polymers and have prompted intensive studies of structure-function relationships in organic electronics 2 , 14 – 16 , 20 , 21 . In particular, taking advantage of the widespread application of palladium-catalyzed polycondensations (including Stille coupling or Suzuki-Miyaura coupling) 1 , 22 , 23 , much efforts have been devoted to developing DP-insensitive polymer donor ( P D ) and polymer acceptor ( P A ) materials in PSCs 24 – 26 . However, the aromaticity and reactivity of conjugated polymers undergo variations with the chain length and pre-aggregation among the living polymer chains during chain-growth polymerization.…”