| Title |
Azobenzene-triindole hybrid chromophores as light-responsive organic semiconductors: synthesis, photoisomerization and semiconducting properties |
| Authors |
Fabregat, Clara ; Garcia-Amorós, Jaume ; Volyniuk, Dmytro ; Grazulevicius, Juozas V ; Velasco, Dolores |
| DOI |
10.1016/j.dyepig.2026.113772 |
| Full Text |
|
| Is Part of |
Dyes and pigments.. London : Elsevier. 2026, vol. 252, art. no. 113772, p. 25066-25074.. ISSN 0143-7208. eISSN 1873-3743 |
| Keywords [eng] |
Azobenzene ; Light-addressable materials ; Organic semiconductors ; Photoresponsive ; Triindole |
| Abstract [eng] |
Azobenzene (AB) chromophores are among the most widely utilized molecular photoswitches; however, their integration into organic semiconductor (OSC) frameworks to enable orthogonal light-driven control of the electronic properties while maintaining efficient charge transport remains a significant challenge. Herein, we report the design and synthesis of a series of novel photoactive OSCs hybrids in which AB units have been integrated into the OSC backbone of 10,15-dihydro-5H-diindolo[3,2-a:3′,2′-c]carbazole, namely triindole. Structural variations involving the number of AB units, their functionalization site and the incorporation of alkoxy spacers have been employed to systematically evaluate and monitor their photophysical and electronic properties. As a result, all the derivatives presented photoactivity, exhibiting a bistable behavior with efficient and reversible photoisomerization in both solution and solid phase under UV or visible light irradiation. Additionally, these materials displayed excellent thermal robustness (Td > 350 °C) and appropriate HOMO-LUMO energy levels for air stable p-type OSCs. Time-of-flight measurements further confirmed efficient hole transport, with mobilities reaching up to 1.5 × 10−4 cm2 V−1 s−1 under an applied electric field of 6 × 105 V cm−1. Hence, the combination of outstanding photoresponsiveness and favorable semiconducting properties establishes these AB-triindole hybrids as promising building blocks for future photoactive and light-addressable electronic devices. |
| Published |
London : Elsevier |
| Type |
Journal article |
| Language |
English |
| Publication date |
2026 |
| CC license |
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