Issue 41, 2022

Thiazole fused S,N-heteroacene step-ladder polymeric semiconductors for organic transistors

Abstract

Ladder-type thiazole-fused S,N-heteroacenes with an extended π-conjugation consisting of six (SN6-Tz) and nine (SN9-Tz) fused aromatic rings have been synthesized and fully characterized. To date, the synthesis of well-defined fused building blocks and polymers of π-conjugated organic compounds based on the thiazole moiety is a considerable synthetic challenge, due to the difficulty in their synthesis. Acceptor–donor building blocks M1 and M2 were successfully polymerized into ladder homopolymers P1–P2 and further copolymerized with a diketopyrrolopyrrole unit to afford step-ladder copolymer P3. The optical, electronic, and thermal properties, in addition to their charge transport behavior in organic thin-film transistors (OTFTs), were investigated. The results showed an interesting effect on the molecular arrangement of the thiazole-based ladder-type heteroacene in the crystal structure revealing skewed π–π-stacking, and expected to possess better p-type semiconducting performance. The polymers all possess good molecular weights and excellent thermal properties. All the polymer-based OTFT devices exhibit annealing temperature dependent performance, and among the polymers P3 exhibits the highest mobility of 0.05 cm2 V−1 s−1.

Graphical abstract: Thiazole fused S,N-heteroacene step-ladder polymeric semiconductors for organic transistors

Supplementary files

Article information

Article type
Edge Article
Submitted
21 avq 2022
Accepted
05 sen 2022
First published
26 sen 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2022,13, 12034-12044

Thiazole fused S,N-heteroacene step-ladder polymeric semiconductors for organic transistors

S. Attar, R. Yang, Z. Chen, X. Ji, M. Comí, S. Banerjee, L. Fang, Y. Liu and M. Al-Hashimi, Chem. Sci., 2022, 13, 12034 DOI: 10.1039/D2SC04661J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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