Benzodicarbomethoxytetrathiafulvalene derivatives as soluble organic semiconductors

Francisco Otón; Raphael Pfattner; Neil S. Oxtoby; Marta Mas-Torrent; Klaus Wurst; Xavier Fontrodona; Yoann Olivier; Jérôme Cornil; Jaume Veciana; Concepció Rovira

doi:10.1021/jo101817j

Benzodicarbomethoxytetrathiafulvalene derivatives as soluble organic semiconductors

Francisco Otón, Raphael Pfattner, Neil S. Oxtoby, Marta Mas-Torrent, Klaus Wurst, Xavier Fontrodona, Yoann Olivier, Jérôme Cornil, Jaume Veciana, Concepció Rovira

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Résumé

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).

langue originale	Anglais
Pages (de - à)	154-163
Nombre de pages	10
journal	Journal of Organic Chemistry
Volume	76
Numéro de publication	1
Les DOIs	https://doi.org/10.1021/jo101817j
Etat de la publication	Publié - 7 janv. 2011
Modification externe	Oui

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10.1021/jo101817j

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abstract = "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).",

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AU - Otón, Francisco

AU - Pfattner, Raphael

AU - Oxtoby, Neil S.

AU - Mas-Torrent, Marta

AU - Wurst, Klaus

AU - Fontrodona, Xavier

AU - Olivier, Yoann

AU - Cornil, Jérôme

AU - Veciana, Jaume

AU - Rovira, Concepció

PY - 2011/1/7

Y1 - 2011/1/7

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AB - 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).

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Benzodicarbomethoxytetrathiafulvalene derivatives as soluble organic semiconductors

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