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

doi:10.1021/jo102066x

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

33 Citations (Scopus)

Abstract

In continuation of previous studies showing promising metal-molecule contact properties a variety of C₆₀ 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 π-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.

Original language	English
Journal	The Journal of Organic Chemistry
Volume	76
Issue number	1
Pages (from-to)	245-63
Number of pages	19
ISSN	0022-3263
DOIs	https://doi.org/10.1021/jo102066x
Publication status	Published - 7 Jan 2011

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Sørensen, J. K., Fock, J., Pedersen, A. H., Petersen, A. B., 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. The Journal of Organic Chemistry, 76(1), 245-63. https://doi.org/10.1021/jo102066x

Fulleropyrrolidine end-capped molecular wires for molecular electronics--synthesis, spectroscopic, electrochemical, and theoretical characterization. / Sørensen, Jakob Kryger; Fock, Jeppe; Pedersen, Anders Holmen et al.

In: The Journal of Organic Chemistry, Vol. 76, No. 1, 07.01.2011, p. 245-63.

Research output: Contribution to journal › Journal article › Research › peer-review

Sørensen, JK, Fock, J, Pedersen, AH, Petersen, AB, Jennum, K, Bechgaard, K, Kilså, K, Geskin, V, Cornil, J, Bjørnholm, T & Nielsen, MB 2011, 'Fulleropyrrolidine end-capped molecular wires for molecular electronics--synthesis, spectroscopic, electrochemical, and theoretical characterization', The Journal of Organic Chemistry, vol. 76, no. 1, pp. 245-63. https://doi.org/10.1021/jo102066x

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title = "Fulleropyrrolidine end-capped molecular wires for molecular electronics--synthesis, spectroscopic, electrochemical, and theoretical characterization",

abstract = "In continuation of previous studies showing promising metal-molecule contact properties a variety of C60 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 π-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.",

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T1 - Fulleropyrrolidine end-capped molecular wires for molecular electronics--synthesis, spectroscopic, electrochemical, and theoretical characterization

AU - Sørensen, Jakob Kryger

AU - Fock, Jeppe

AU - Pedersen, Anders Holmen

AU - Petersen, Asger B

AU - Jennum, Karsten

AU - Bechgaard, Klaus

AU - Kilså, Kristine

AU - Geskin, Victor

AU - Cornil, Jérôme

AU - Bjørnholm, Thomas

AU - Nielsen, Mogens Brøndsted

PY - 2011/1/7

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N2 - In continuation of previous studies showing promising metal-molecule contact properties a variety of C60 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 π-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.

AB - In continuation of previous studies showing promising metal-molecule contact properties a variety of C60 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 π-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.

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DO - 10.1021/jo102066x

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VL - 76

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EP - 263

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 1

ER -

Fulleropyrrolidine end-capped molecular wires for molecular electronics--synthesis, spectroscopic, electrochemical, and theoretical characterization

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