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Design and Synthesis of Aviram-Ratner-Type Dyads and Rectification Studies in Langmuir-Blodgett (LB) Films.

  • Jayamurugan G Laboratorium für Organische Chemie, ETH Zurich, Vladimir-Prelog-Weg 3, 8093, Zurich, Switzerland), Fax: (+41) 44-632-1109.
  • Gowri V Laboratorium für Organische Chemie, ETH Zurich, Vladimir-Prelog-Weg 3, 8093, Zurich, Switzerland), Fax: (+41) 44-632-1109.
  • Hernández D Departamento de Química Física, Facultad de Ciencias, Universidad de Zaragoza, 50009, Zaragoza, Spain), Fax: (+34) 976-761-202.
  • Martin S Departamento de Química Física, Facultad de Ciencias, Universidad de Zaragoza, 50009, Zaragoza, Spain), Fax: (+34) 976-761-202.
  • González-Orive A Instituto de Nanociencia de Aragón (INA) and Laboratorio de Microscopias Avanzadas (LMA), Edificio i+d. Campus Rio Ebro, Universidad de Zaragoza, C/Mariano Esquillor, s/n, 50017, Zaragoza, Spain.
  • Dengiz C Laboratorium für Organische Chemie, ETH Zurich, Vladimir-Prelog-Weg 3, 8093, Zurich, Switzerland), Fax: (+41) 44-632-1109.
  • Dumele O Laboratorium für Organische Chemie, ETH Zurich, Vladimir-Prelog-Weg 3, 8093, Zurich, Switzerland), Fax: (+41) 44-632-1109.
  • Pérez-Murano F Instituto de Microelectrónica de Barcelona (IMB-CNM, CSIC), Campus UAB, 08193, Bellaterra, Spain.
  • Gisselbrecht JP Laboratoire d'Electrochimie et de Chimie Physique du Corps Solide, Institut de Chimie-UMR 7177, C.N.R.S., Université de Strasbourg, 4 rue Blaise Pascal, CS 90032, 67081, Strasbourg Cedex, France.
  • Boudon C Laboratoire d'Electrochimie et de Chimie Physique du Corps Solide, Institut de Chimie-UMR 7177, C.N.R.S., Université de Strasbourg, 4 rue Blaise Pascal, CS 90032, 67081, Strasbourg Cedex, France.
  • Schweizer WB Laboratorium für Organische Chemie, ETH Zurich, Vladimir-Prelog-Weg 3, 8093, Zurich, Switzerland), Fax: (+41) 44-632-1109.
  • Breiten B Laboratorium für Organische Chemie, ETH Zurich, Vladimir-Prelog-Weg 3, 8093, Zurich, Switzerland), Fax: (+41) 44-632-1109.
  • Finke AD Laboratorium für Organische Chemie, ETH Zurich, Vladimir-Prelog-Weg 3, 8093, Zurich, Switzerland), Fax: (+41) 44-632-1109.
  • Jeschke G Laboratory of Physical Chemistry, ETH Zurich, Vladimir-Prelog-Weg 2, 8093, Zurich, Switzerland.
  • Bernet B Laboratorium für Organische Chemie, ETH Zurich, Vladimir-Prelog-Weg 3, 8093, Zurich, Switzerland), Fax: (+41) 44-632-1109.
  • Ruhlmann L Laboratoire d'Electrochimie et de Chimie Physique du Corps Solide, Institut de Chimie-UMR 7177, C.N.R.S., Université de Strasbourg, 4 rue Blaise Pascal, CS 90032, 67081, Strasbourg Cedex, France.
  • Cea P Departamento de Química Física, Facultad de Ciencias, Universidad de Zaragoza, 50009, Zaragoza, Spain), Fax: (+34) 976-761-202. pilarcea@unizar.es.
  • Diederich F Laboratorium für Organische Chemie, ETH Zurich, Vladimir-Prelog-Weg 3, 8093, Zurich, Switzerland), Fax: (+41) 44-632-1109. diederich@org.chem.ethz.ch.
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  • 2016-07-02
Published in:
  • Chemistry (Weinheim an der Bergstrasse, Germany). - 2016
Aviram-Ratner dyad
Langmuir-Blodgett films
[2+2] cycloaddition-retroelectrocyclization
charge transfer
molecular electronics materials
English The 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.
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  • English
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green
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https://sonar.ch/global/documents/100938
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