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

Ladder-type thiazole-fused S,N-heteroacenes with an extended pi-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 pi-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 pi-pi-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 cm(2) V-1 s(-1).

Automated summary

Ladder-type thiazole-fused S,N-heteroacenes with extended pi-conjugation have been synthesized and characterized. These compounds exhibit good optical, electronic, and thermal properties and show promising charge transport behavior in organic thin-film transistors.