Dihydroazulene-Buckminsterfullerene Conjugates

Marco Santella, Virginia Mazzanti, Martyn Jevric, C. R. Parker, Søren Lindbæk Broman, A. D. Bond, M. B. Nielsen

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

The dihydroazulene (DHA)/vinylheptafulvene (VHF) photo/thermoswitch has recently attracted interest as a molecular switch for molecular electronics. In this field, Buckminsterfullerene, C-60, has been shown to be a useful anchoring group for adhering a molecular wire to an electrode. Here we have combined the two units with the overall aim to elucidate how C-60 influences the DHA-VHF switching events. Efficient synthetic protocols for making covalently linked DHA-C-60 conjugates were developed, using Prato, Sonogashira, Hay, and Cadiot-Chodkiewicz reactions. These syntheses provide as well a variety of potentially useful DHA and C-60 building blocks for acetylenic scaffolding. The two units were separated by bridges of various lengths, such as oligo(phenyleneethynylene) (OPE2 and OPE3) wires. The distance of separation was found to influence strongly the light induced ring opening reaction Of DHA to its corresponding VHF. Thus, C-60 was found to significantly quench this conversion when situated closely to the DHA unit
OriginalsprogEngelsk
TidsskriftJournal of Organic Chemistry
Vol/bind77
Udgave nummer20
Sider (fra-til)8922-8932
Antal sider11
ISSN0022-3263
DOI
StatusUdgivet - 2012

Citer dette

Santella, M., Mazzanti, V., Jevric, M., Parker, C. R., Broman, S. L., Bond, A. D., & Nielsen, M. B. (2012). Dihydroazulene-Buckminsterfullerene Conjugates. Journal of Organic Chemistry, 77(20), 8922-8932. https://doi.org/10.1021/jo301306y
Santella, Marco ; Mazzanti, Virginia ; Jevric, Martyn ; Parker, C. R. ; Broman, Søren Lindbæk ; Bond, A. D. ; Nielsen, M. B. / Dihydroazulene-Buckminsterfullerene Conjugates. I: Journal of Organic Chemistry. 2012 ; Bind 77, Nr. 20. s. 8922-8932.
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abstract = "The dihydroazulene (DHA)/vinylheptafulvene (VHF) photo/thermoswitch has recently attracted interest as a molecular switch for molecular electronics. In this field, Buckminsterfullerene, C-60, has been shown to be a useful anchoring group for adhering a molecular wire to an electrode. Here we have combined the two units with the overall aim to elucidate how C-60 influences the DHA-VHF switching events. Efficient synthetic protocols for making covalently linked DHA-C-60 conjugates were developed, using Prato, Sonogashira, Hay, and Cadiot-Chodkiewicz reactions. These syntheses provide as well a variety of potentially useful DHA and C-60 building blocks for acetylenic scaffolding. The two units were separated by bridges of various lengths, such as oligo(phenyleneethynylene) (OPE2 and OPE3) wires. The distance of separation was found to influence strongly the light induced ring opening reaction Of DHA to its corresponding VHF. Thus, C-60 was found to significantly quench this conversion when situated closely to the DHA unit",
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Santella, M, Mazzanti, V, Jevric, M, Parker, CR, Broman, SL, Bond, AD & Nielsen, MB 2012, 'Dihydroazulene-Buckminsterfullerene Conjugates', Journal of Organic Chemistry, bind 77, nr. 20, s. 8922-8932. https://doi.org/10.1021/jo301306y

Dihydroazulene-Buckminsterfullerene Conjugates. / Santella, Marco; Mazzanti, Virginia; Jevric, Martyn; Parker, C. R.; Broman, Søren Lindbæk; Bond, A. D.; Nielsen, M. B.

I: Journal of Organic Chemistry, Bind 77, Nr. 20, 2012, s. 8922-8932.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Dihydroazulene-Buckminsterfullerene Conjugates

AU - Santella, Marco

AU - Mazzanti, Virginia

AU - Jevric, Martyn

AU - Parker, C. R.

AU - Broman, Søren Lindbæk

AU - Bond, A. D.

AU - Nielsen, M. B.

PY - 2012

Y1 - 2012

N2 - The dihydroazulene (DHA)/vinylheptafulvene (VHF) photo/thermoswitch has recently attracted interest as a molecular switch for molecular electronics. In this field, Buckminsterfullerene, C-60, has been shown to be a useful anchoring group for adhering a molecular wire to an electrode. Here we have combined the two units with the overall aim to elucidate how C-60 influences the DHA-VHF switching events. Efficient synthetic protocols for making covalently linked DHA-C-60 conjugates were developed, using Prato, Sonogashira, Hay, and Cadiot-Chodkiewicz reactions. These syntheses provide as well a variety of potentially useful DHA and C-60 building blocks for acetylenic scaffolding. The two units were separated by bridges of various lengths, such as oligo(phenyleneethynylene) (OPE2 and OPE3) wires. The distance of separation was found to influence strongly the light induced ring opening reaction Of DHA to its corresponding VHF. Thus, C-60 was found to significantly quench this conversion when situated closely to the DHA unit

AB - The dihydroazulene (DHA)/vinylheptafulvene (VHF) photo/thermoswitch has recently attracted interest as a molecular switch for molecular electronics. In this field, Buckminsterfullerene, C-60, has been shown to be a useful anchoring group for adhering a molecular wire to an electrode. Here we have combined the two units with the overall aim to elucidate how C-60 influences the DHA-VHF switching events. Efficient synthetic protocols for making covalently linked DHA-C-60 conjugates were developed, using Prato, Sonogashira, Hay, and Cadiot-Chodkiewicz reactions. These syntheses provide as well a variety of potentially useful DHA and C-60 building blocks for acetylenic scaffolding. The two units were separated by bridges of various lengths, such as oligo(phenyleneethynylene) (OPE2 and OPE3) wires. The distance of separation was found to influence strongly the light induced ring opening reaction Of DHA to its corresponding VHF. Thus, C-60 was found to significantly quench this conversion when situated closely to the DHA unit

U2 - 10.1021/jo301306y

DO - 10.1021/jo301306y

M3 - Journal article

VL - 77

SP - 8922

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

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Santella M, Mazzanti V, Jevric M, Parker CR, Broman SL, Bond AD et al. Dihydroazulene-Buckminsterfullerene Conjugates. Journal of Organic Chemistry. 2012;77(20):8922-8932. https://doi.org/10.1021/jo301306y