Fulleropyrrolidine End-Capped Molecular Wires for Molecular Electronics—Synthesis, Spectroscopic, Electrochemical, and Theoretical Characterization

Jakob Kryger Sørensen, Jeppe Fock, Anders Holmen Pedersen, Asger B. Petersen, Karsten Jennum, Klaus Bechgaard, Kristine Kilså, Victor Geskin, Jérôme Cornil, Thomas Bjørnholm, Mogens Brøndsted Nielsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

In continuation of previous studies showing promising metal molecule contact properties a variety of C-60 end-capped "molecular wires" for molecular electronics were prepared by variants of the Prato 1,3-dipolar cycloaddition reaction. Either benzene or fluorene was chosen as the central wire, and synthetic protocols for derivatives terminated with one or two fullero[c]pyrrolidine "electrode anchoring" groups were developed. An aryl-substituted aziridine could in some cases be employed directly as the azomethine ylide precursor for the Prato reaction without the need of having an electron-withdrawing ester group present. The effect of extending the pi-system of the central wire from 1,4-phenylenediamine to 2,7-fluorenediamine was investigated by absorption, fluorescence, and electrochemical methods. The central wire and the Co-60 end-groups were found not to electronically communicate in the ground state. However, the fluorescence of C60 was quenched by charge transfer from the wire to C-60. Quantum chemical calculations predict and explain the collapse of coherent electronic transmission through one of the fulleropyrrolidine-terminated molecular wires.
Original languageEnglish
JournalJournal of Organic Chemistry
Volume76
Issue number1
Pages (from-to)245-263
ISSN0022-3263
DOIs
Publication statusPublished - 2011
Externally publishedYes

Cite this

Sørensen, J. K., Fock, J., Holmen Pedersen, A., B. Petersen, A., Jennum, K., Bechgaard, K., Kilså, K., Geskin, V., Cornil, J., Bjørnholm, T., & Nielsen, M. B. (2011). Fulleropyrrolidine End-Capped Molecular Wires for Molecular Electronics—Synthesis, Spectroscopic, Electrochemical, and Theoretical Characterization. Journal of Organic Chemistry, 76(1), 245-263. https://doi.org/10.1021/jo102066x