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A Trapezoidal Octacyanoquinoid Acceptor Forms Solution and Surface Products by Antiparallel Shape Fitting with
Samara Medina Rivero1, Javier Urieta-Mora2,3, Agustín Molina-Ontoria2
1Department of Physical Chemistry, University of Málaga, Andalucia-Tech Campus de Teatinos s/n, 29071, Málaga, Spain.
Abstract:
A new compound (1) formed by two antiparallelly disposed tetracyano thienoquinoidal units has been synthesized and studied by electrochemistry, UV/Vis-NIR, IR, EPR, and transient spectroscopy. Self-assembly of 1 on a Au(111) surface has been investigated by scanning tunneling microscopy. Experiments have been rationalized by quantum chemical calculations. 1 exhibits a unique charge distribution in its anionic form, with a gradient of charge yielding a neat molecular in-plane electric dipole momentum, which transforms out-of-plane after surface deposition due to twisted→folded conformational change and to partial charge transfer from Au(111). Intermolecular van der Waals interactions and antiparallel trapezoidal shape fitting lead to the formation of an optimal dense on Au(111) two-dimensional assembly of 1.
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