Electron-withdrawing substituted tetrathiafulvalenes as ambipolar semiconductors

The synthesis of four new TTF derivatives bearing phthalimides and fluorinated alkyl moieties as potential ambipolar semiconductors is described. The presence of such electron-withdrawing groups permits the stabilization of the energy of HOMO and LUMO orbitals. The solid-state structures of these no...

Descripción completa

Detalles Bibliográficos
Autores: Otón, Francisco, Pfattner, Raphael, Pavlica, Egon, Olivier, Yoann, Moreno Calvo, Evelyn, Puigdollers-González, Joaquim, Bratina, Gvido, Cornil, Jérôme, Fontrodona, Xavier, Mas Torrent, Marta, 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:10261/102948
Acceso en línea:http://hdl.handle.net/10261/102948
Access Level:acceso abierto
Palabra clave:Single-crystals
Carrier type
Dithiophene-tetrathiafulvalene
High-performance
Organic semiconductors
Field-effect transistors
Powder diffracton data
Thin-film transistors
Monte-Carlo methods
Charge-transport
id ES_bd36713beef0a8f1d77983ea2ce32c55
oai_identifier_str oai:digital.csic.es:10261/102948
network_acronym_str ES
network_name_str España
repository_id_str
spelling Electron-withdrawing substituted tetrathiafulvalenes as ambipolar semiconductorsOtón, FranciscoPfattner, RaphaelPavlica, EgonOlivier, YoannMoreno Calvo, EvelynPuigdollers-González, JoaquimBratina, GvidoCornil, JérômeFontrodona, XavierMas Torrent, MartaVeciana, JaumeRovira, ConcepcióSingle-crystalsCarrier typeDithiophene-tetrathiafulvaleneHigh-performanceOrganic semiconductorsField-effect transistorsPowder diffracton dataThin-film transistorsMonte-Carlo methodsCharge-transportThe synthesis of four new TTF derivatives bearing phthalimides and fluorinated alkyl moieties as potential ambipolar semiconductors is described. The presence of such electron-withdrawing groups permits the stabilization of the energy of HOMO and LUMO orbitals. The solid-state structures of these novel molecules have been characterized by X-ray diffraction techniques. The potential of these materials as hole and electron conductors has been estimated under theoretical considerations by evaluating the position of the frontier energy levels as well as their charge carrier mobilities. Preparation of solution-processed single crystal organic field-effect transistors (OFETs) has resulted in hole mobilities of up to 0.33 cm2 V-1 s -1 for compound 1. On the other hand, electrical time of flight (EToF) measurements on single crystals of compound 3 demonstrated ambipolar transport, reaching very high mobility values around 2.0 cm2 V -1 s-1 for both types of charges. © 2010 American Chemical Society.The research leading to these results has received funding from the European Community's Seventh Framework Programme (FP7/2007-2013) under grant agreement n° 212311 of the ONE-P project, Marie Curie EST FuMASSEC, DGI, Spain (contracts CTQ2006-06333/BQU and CTQ2010-195011/BQU), the Generalitat de Catalunya, (2009SGR00516) and the program “Juan de la Cierva”(MICINN). We also thank Stefan T. Bromley for his advice regarding the DFT calculations and CESGA for the use of their computational resources. The work in Mons is also supported by the European ONE-P project as well as by the Belgian National Fund for Scientific Research (FNRS). Y.O. and J.C. are FNRS research fellows. Peer ReviewedAmerican Chemical Society2014201420112014info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501http://hdl.handle.net/10261/102948reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/EC/FP7/212311info:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1029482026-05-22T06:33:51Z
dc.title.none.fl_str_mv Electron-withdrawing substituted tetrathiafulvalenes as ambipolar semiconductors
title Electron-withdrawing substituted tetrathiafulvalenes as ambipolar semiconductors
spellingShingle Electron-withdrawing substituted tetrathiafulvalenes as ambipolar semiconductors
Otón, Francisco
Single-crystals
Carrier type
Dithiophene-tetrathiafulvalene
High-performance
Organic semiconductors
Field-effect transistors
Powder diffracton data
Thin-film transistors
Monte-Carlo methods
Charge-transport
title_short Electron-withdrawing substituted tetrathiafulvalenes as ambipolar semiconductors
title_full Electron-withdrawing substituted tetrathiafulvalenes as ambipolar semiconductors
title_fullStr Electron-withdrawing substituted tetrathiafulvalenes as ambipolar semiconductors
title_full_unstemmed Electron-withdrawing substituted tetrathiafulvalenes as ambipolar semiconductors
title_sort Electron-withdrawing substituted tetrathiafulvalenes as ambipolar semiconductors
dc.creator.none.fl_str_mv Otón, Francisco
Pfattner, Raphael
Pavlica, Egon
Olivier, Yoann
Moreno Calvo, Evelyn
Puigdollers-González, Joaquim
Bratina, Gvido
Cornil, Jérôme
Fontrodona, Xavier
Mas Torrent, Marta
Veciana, Jaume
Rovira, Concepció
author Otón, Francisco
author_facet Otón, Francisco
Pfattner, Raphael
Pavlica, Egon
Olivier, Yoann
Moreno Calvo, Evelyn
Puigdollers-González, Joaquim
Bratina, Gvido
Cornil, Jérôme
Fontrodona, Xavier
Mas Torrent, Marta
Veciana, Jaume
Rovira, Concepció
author_role author
author2 Pfattner, Raphael
Pavlica, Egon
Olivier, Yoann
Moreno Calvo, Evelyn
Puigdollers-González, Joaquim
Bratina, Gvido
Cornil, Jérôme
Fontrodona, Xavier
Mas Torrent, Marta
Veciana, Jaume
Rovira, Concepció
author2_role author
author
author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Single-crystals
Carrier type
Dithiophene-tetrathiafulvalene
High-performance
Organic semiconductors
Field-effect transistors
Powder diffracton data
Thin-film transistors
Monte-Carlo methods
Charge-transport
topic Single-crystals
Carrier type
Dithiophene-tetrathiafulvalene
High-performance
Organic semiconductors
Field-effect transistors
Powder diffracton data
Thin-film transistors
Monte-Carlo methods
Charge-transport
description The synthesis of four new TTF derivatives bearing phthalimides and fluorinated alkyl moieties as potential ambipolar semiconductors is described. The presence of such electron-withdrawing groups permits the stabilization of the energy of HOMO and LUMO orbitals. The solid-state structures of these novel molecules have been characterized by X-ray diffraction techniques. The potential of these materials as hole and electron conductors has been estimated under theoretical considerations by evaluating the position of the frontier energy levels as well as their charge carrier mobilities. Preparation of solution-processed single crystal organic field-effect transistors (OFETs) has resulted in hole mobilities of up to 0.33 cm2 V-1 s -1 for compound 1. On the other hand, electrical time of flight (EToF) measurements on single crystals of compound 3 demonstrated ambipolar transport, reaching very high mobility values around 2.0 cm2 V -1 s-1 for both types of charges. © 2010 American Chemical Society.
publishDate 2011
dc.date.none.fl_str_mv 2011
2014
2014
2014
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/102948
url http://hdl.handle.net/10261/102948
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/EC/FP7/212311
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869418181839290368
score 15,811543

Similares en LA Referencia