RT Journal Article
T1 [2,2′]Paracyclophane-Based π-Conjugated Molecular Wires Reveal Molecular-Junction Behavior
A1 Molina Ontoria, Agustín
A1 Wielopolski, Mateusz
A1 Gebhardt, Julian
A1 Gouloumis, Andreas
A1 Clark, Timothy
A1 Guldi, Dirk M.
A1 Martín León, Nazario
AB The electronic coupling as well as the attenuation factor (β), which depends primarily on the nature of the molecular bridge and is used as a benchmark to test the molecular wire behavior, have been determined in a systematic study carried out on a series of ZnP/C60 conjugates connected through a [2,20]paracyclophaneoligophenylenevinylene (pCp-oPPV). The convergent synthesis involves a series of Horner-Emmons olefination reactions or double palladium-catalized Heck-type reactions. ZnP-pCp-C60 conjugates were finally obtained by the 1,3-dipolar cycloaddition reaction of the in situ-generated azomethyne ylide containing the ZnP-pCp moiety to the [60]fullerene using Prato conditions. Experimental (UV-vis, fluorescence, transient absorption spectroscopy, and solution electrochemistry) and theoretical studies revealed that the pCps act as molecular junctions. If hole transfer is assumed to be the dominant charge transfer (CT) mechanism, CT is facilitated in one direction (from C60 to ZnP via pCp) but disfavored in the other direction (from ZnP to C60 via pCp).
PB AMERICAN CHEMICAL SOCIETY
SN 0002-7863
SN 1520-5126
YR 2011
FD 2011-02-07
LK https://hdl.handle.net/20.500.14352/114302
UL https://hdl.handle.net/20.500.14352/114302
LA eng
NO Agustín Molina-Ontoria, Mateusz Wielopolski, Julian Gebhardt, Andreas Gouloumis, Timothy Clark, Dirk M. Guldi, and Nazario Martín Journal of the American Chemical Society 2011 133 (8), 2370-2373 DOI: 10.1021/ja109745a
NO Ministerio de Educación
NO Comunidad de Madrid
NO European Commission
NO Deutsche Forschungsge-meinschaft
DS Docta Complutense
RD 10 abr 2025