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Design and synthesis of Aviram-Ratner-type dyads and rectification studies in Langmuir-Blodgett (LB) films

AutorMartín, Santiago; González-Orive, Alejandro; Perez Murano, Francesc X. ; Cea, Pilar; Diederich, François
Palabras clave[2+2] cycloaddition–retroelectrocyclization
Charge transfer
Molecular electronics materials
Langmuir–Blodgett films
Aviram–Ratner dyad
Fecha de publicación2016
EditorWiley-VCH
CitaciónChemistry - A European Journal 22(30): 10539-10547 (2016)
ResumenThe design and synthesis of Aviram–Ratner-type molecular rectifiers, featuring an anilino-substituted extended tetracyanoquinodimethane (exTCNQ) acceptor, covalently linked by the σ-spacer bicyclo[2.2.2]octane (BCO) to a tetrathiafulvalene (TTF) donor moiety, are described. The rigid BCO spacer keeps the TTF donor and exTCNQ acceptor moieties apart, as demonstrated by X-ray analysis. The photophysical properties of the TTF-BCO-exTCNQ dyads were investigated by UV/Vis and EPR spectroscopy, electrochemical studies, and theoretical calculations. Langmuir–Blodgett films were prepared and used in the fabrication and electrical studies of junction devices. One dyad showed the asymmetric current–voltage (I–V) curve characteristic for rectification, unlike control compounds containing the TTF unit but not the exTCNQ moiety or comprising the exTCNQ acceptor moiety but lacking the donor TTF part, which both gave symmetric I–V curves. The direction of the observed rectification indicated that the preferred electron current flows from the exTCNQ acceptor to the TTF donor.
Versión del editorhttps://doi.org/10.1002/chem.201505216
URIhttp://hdl.handle.net/10261/148498
DOI10.1002/chem.201505216
Identificadoresdoi: 10.1002/chem.201505216
e-issn: 1521-3765
issn: 0947-6539
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