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

Research output: Contribution to journal › Article › peer-review

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).

Original language	English
Pages (from-to)	154-163
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	76
Issue number	1
DOIs	https://doi.org/10.1021/jo101817j
Publication status	Published - 7 Jan 2011
Externally published	Yes

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title = "Benzodicarbomethoxytetrathiafulvalene derivatives as soluble organic semiconductors",

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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doi = "10.1021/jo101817j",

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T1 - Benzodicarbomethoxytetrathiafulvalene derivatives as soluble organic semiconductors

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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JO - Journal of Organic Chemistry

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Benzodicarbomethoxytetrathiafulvalene derivatives as soluble organic semiconductors

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