Fulleropyrrolidine End-Capped Molecular Wires for Molecular Electronics鈥擲ynthesis, Spectroscopic, Electrochemical, and Theoretical Characterization

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• 作者：Jakob Kryger S酶rensen ; Jeppe Fock ; Anders Holmen Pedersen ; Asger B. Petersen ; Karsten Jennum ; Klaus Bechgaard ; Kristine Kilsa虋 ; Victor Geskin ; Je虂ro虃me Cornil ; Thomas Bj酶rnholm ; Mogens Br酶ndsted Nielsen
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：January 7, 2011
• 年：2011
• 卷：76
• 期：1
• 页码：245-263
• 全文大小：1583K
• 年卷期：v.76,no.1(January 7, 2011)
• ISSN：1520-6904

文摘

In continuation of previous studies showing promising metal鈭抦olecule contact properties a variety of C₆₀ end-capped 鈥渕olecular wires鈥?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 鈥渆lectrode anchoring鈥?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 蟺-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 C₆₀ 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 C₆₀. Quantum chemical calculations predict and explain the collapse of coherent electronic transmission through one of the fulleropyrrolidine-terminated molecular wires.