Benzodicarbomethoxytetrathiafulvalene derivatives as soluble organic semiconductors

A series of new tetrathiafulvalene (TTF) derivatives bearing dimethoxycarbonyl and phenyl or phthalimidyl groups fused to the TTF core (6 and 15-18) has been synthesized as potential soluble semiconductor materials for organic field-effect transistors (OFETs). The electron-withdrawing substituents l...

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Detalles Bibliográficos
Autores: Otón, Francisco, Pfattner, Raphael, Oxtoby, Neil S., Mas Torrent, Marta, Wurst, Klaus, Fontrodona, Xavier, Olivier, Yoann, Cornil, Jérôme, Veciana, Jaume, Rovira, Concepció
Tipo de recurso: artículo
Fecha de publicación:2011
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/102932
Acceso en línea:http://hdl.handle.net/10261/102932
Access Level:acceso abierto
Palabra clave:Dithiophene-tetrathiafulvalene
High-mobility
Charge-transsport
Extended tetrathialfulvalene derivatives
Field-effect transistors
Energy
Single-crystals
Intermolecular interactions
Photophysical properties
Electron-transfer
Descripción
Sumario:A series of new tetrathiafulvalene (TTF) derivatives bearing dimethoxycarbonyl and phenyl or phthalimidyl groups fused to the TTF core (6 and 15-18) has been synthesized as potential soluble semiconductor materials for organic field-effect transistors (OFETs). The electron-withdrawing substituents lower the energy of the HOMO and LUMO levels and increase the solubility and stability of the semiconducting material. Crystal structures of all new TTF derivatives are also described, and theoretical DFT calculations were carried out to study the potential of the crystals to be used in OFET. In the experimental study, the best performing device exhibited a hole mobility up to 7.5 × 10-3 cm2 V-1 s-1). © 2010 American Chemical Society.