Low-bandgap oligothiophene-naphthalimide oligomeric semiconductors for thermoelectric applications
Journal article, 2025
State-of-the-art p-type organic conjugated polymers are mostly thiophene-based semiconductors. Still, novel chemical design and a fresh perspective on different polymer backbones could pave the way for new high-performing materials and a deep understanding of donor-acceptor conjugated assemblies. Herein we designed and synthesized two novel electroactive oligomeric materials based on a donor terthiophene unit endowed with a strong electron-withdrawing naphthalimide unit. This molecular assembly has been polymerized using a palladium cross-coupling reaction with two different linkers, 1,1,1,2,2,2-hexabutyldistannane and (4,8-bis((2-ethylhexyl)oxy)benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl)bis(trimethylstannane), to obtain the target polymers NIP3T-poly and NIP3T-BDT-poly, respectively. Both polymers exhibited an extended absorption up to 1000 nm and higher hole field-effect mobilities of up to 1.8 × 10−3 cm2 V−1 s−1, in comparison to the molecular assembly NIP3T, and precisely tuned energy levels that make them compatible with common p-type dopants like 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ). After optimizing the doping level, we obtained a thermoelectric figure of merit up to zT = 0.02 for NIP3T-BDT-poly, comparable with benchmark F4TCNQ-vapor doped polythiophenes.
Author
Matías J. Alonso-Navarro
Rey Juan Carlos University (URJC)
Complutense University
Osnat Zapata-Arteaga
Spanish National Research Council (CSIC)
Sergi Riera-Galindo
Spanish National Research Council (CSIC)
Jiali Guo
Spanish National Research Council (CSIC)
None Aleksandr-Peredeventsv
Spanish National Research Council (CSIC)
Edgar Gutiérrez-Fernández
University of the Basque Country (UPV/EHU)
Juan Sebastián Reparaz
Spanish National Research Council (CSIC)
Mar Ramos
Rey Juan Carlos University (URJC)
Christian Müller
Chalmers, Chemistry and Chemical Engineering, Applied Chemistry
Jaime Martín
University of the Basque Country (UPV/EHU)
Marta Mas-Torrent
Spanish National Research Council (CSIC)
José L. Segura
Complutense University
M. Campoy-Quiles
Spanish National Research Council (CSIC)
Journal of Materials Chemistry C
20507526 (ISSN) 20507534 (eISSN)
Vol. In PressSubject Categories (SSIF 2025)
Materials Chemistry
Polymer Chemistry
Condensed Matter Physics
DOI
10.1039/d4tc05383d