[2,2]Paracyclophane-Based π-Conjugated Molecular Wires Reveal Molecular-Junction Behavior
Molina-Ontoria A, Wielopolski M, Gebhardt J, Gouloumis A, Clark T, Guldi DM, Martin N (2011)
Publication Type: Journal article
Publication year: 2011
Journal
Book Volume: 133
Pages Range: 2370-2373
Journal Issue: 8
DOI: 10.1021/ja109745a
Abstract
The electronic coupling as well as the attenuation factor (\textgreekb), 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 [2,2$\prime$]paracyclophane$-$oligophenylenevinylene (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).
Authors with CRIS profile
Julian Gebhardt
Sonderforschungsbereich 953/3 Synthetische Kohlenstoffallotrope
Timothy Clark
Computer-Chemie-Centrum
Dirk Michael Guldi
Lehrstuhl für Physikalische Chemie I
Additional Organisation(s)
Involved external institutions
Spain (ES)How to cite
APA:
Molina-Ontoria, A., Wielopolski, M., Gebhardt, J., Gouloumis, A., Clark, T., Guldi, D.M., & Martin, N. (2011). [2,2]Paracyclophane-Based π-Conjugated Molecular Wires Reveal Molecular-Junction Behavior. Journal of the American Chemical Society, 133(8), 2370-2373. https://doi.org/10.1021/ja109745a
MLA:
Molina-Ontoria, Agustin, et al. "[2,2]Paracyclophane-Based π-Conjugated Molecular Wires Reveal Molecular-Junction Behavior." Journal of the American Chemical Society 133.8 (2011): 2370-2373.
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