Fulleropyrrolidine end-capped molecular wires for molecular electronics--synthesis, spectroscopic, electrochemical, and theoretical characterization
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Fulleropyrrolidine end-capped molecular wires for molecular electronics--synthesis, spectroscopic, electrochemical, and theoretical characterization. / Sørensen, Jakob Kryger; Fock, Jeppe; Pedersen, Anders Holmen; Petersen, Asger B; Jennum, Karsten; Bechgaard, Klaus; Kilså, Kristine; Geskin, Victor; Cornil, Jérôme; Bjørnholm, Thomas; Nielsen, Mogens Brøndsted.
I: The Journal of Organic Chemistry, Bind 76, Nr. 1, 07.01.2011, s. 245-63.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
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
Y1 - 2011/1/7
N2 - 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 p-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 C(60) end-groups were found not to electronically communicate in the ground state. However, the fluorescence of C(60) 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.
AB - 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 p-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 C(60) end-groups were found not to electronically communicate in the ground state. However, the fluorescence of C(60) 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.
U2 - 10.1021/jo102066x
DO - 10.1021/jo102066x
M3 - Journal article
C2 - 21133403
VL - 76
SP - 245
EP - 263
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 1
ER -
ID: 33693295