Issue 47, 2022

Structural influences of proquinoidal acceptor moieties on transistor performance and doping capability for diketopyrrolopyrrole-based dual-acceptor conjugated polymers

Abstract

In this study, we design and synthesize three DPP-based dual-acceptor conjugated polymers comprising different proquinoidal heterocyclic acceptors, including benzobisthiadizole (SS), triazolobenzothiadiazole (NS), and benzobistriazole (NN), and investigate their structure–property relationship using a transistor and their conductive states by doping. Owing to the high-spin and proquinoidal characteristics of the NN/NS/SS units, all the prepared polymers possess free radicals. However, a subtle difference in the proquinoidal characteristics among these acceptor units results in varied backbone rigidity and coplanarity of the derived polymers. DPP-NS and DPP-NN are shown to possess better solid-state stacking and crystallinity than DPP-SS, conferred by the alkyl side chains on the triazole unit. Hence, DPP-NS and DPP-NN can deliver enhanced mobilities of 3.0 × 10−2 and 5.3 × 10−2 cm2 V−1 s−1, respectively, after appropriate thermal annealing whereas the stiff DPP-SS only shows a minor improvement. Furthermore, the intrinsic intense radical characteristic of the NN unit is shown to facilitate the receivability of dopants. At a low doping concentration, DPP-NN delivers the highest conductivity of 23.8 S cm−1 among these polymers. Besides, owing to the higher degree of flexibility in chain packing and associated chain aggregation, DPP-NN displays a superior capability to resist the structural deconstruction in the doping state at a high concentration compared to DPP-NS and DPP-SS. Concisely, our results unravel the non-trivial influence of a proquinoidal acceptor moiety on transistor performance and doping capability of the derived polymers.

Graphical abstract: Structural influences of proquinoidal acceptor moieties on transistor performance and doping capability for diketopyrrolopyrrole-based dual-acceptor conjugated polymers

Supplementary files

Article information

Article type
Paper
Submitted
20 sep. 2022
Accepted
09 nov. 2022
First published
10 nov. 2022

J. Mater. Chem. C, 2022,10, 17936-17944

Structural influences of proquinoidal acceptor moieties on transistor performance and doping capability for diketopyrrolopyrrole-based dual-acceptor conjugated polymers

Y. Wu, J. Li, C. Chang, W. He, T. Michinobu, Y. Lin, W. Chen and C. Chueh, J. Mater. Chem. C, 2022, 10, 17936 DOI: 10.1039/D2TC03956G

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