Dihydroazulene-buckminsterfullerene conjugates

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Standard

Dihydroazulene-buckminsterfullerene conjugates. / Santella, Marco; Mazzanti, Virginia; Jevric, Martyn; Parker, Christian Richard; Broman, Søren Lindbæk; Bond, Andrew; Nielsen, Mogens Brøndsted.

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

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Santella, M, Mazzanti, V, Jevric, M, Parker, CR, Broman, SL, Bond, A & Nielsen, MB 2012, 'Dihydroazulene-buckminsterfullerene conjugates', Journal of Organic Chemistry, bind 77, nr. 20, s. 8922-8932. https://doi.org/10.1021/jo301306y

APA

Santella, M., Mazzanti, V., Jevric, M., Parker, C. R., Broman, S. L., Bond, A., & Nielsen, M. B. (2012). Dihydroazulene-buckminsterfullerene conjugates. Journal of Organic Chemistry, 77(20), 8922-8932. https://doi.org/10.1021/jo301306y

Vancouver

Santella M, Mazzanti V, Jevric M, Parker CR, Broman SL, Bond A o.a. Dihydroazulene-buckminsterfullerene conjugates. Journal of Organic Chemistry. 2012;77(20):8922-8932. https://doi.org/10.1021/jo301306y

Author

Santella, Marco ; Mazzanti, Virginia ; Jevric, Martyn ; Parker, Christian Richard ; Broman, Søren Lindbæk ; Bond, Andrew ; Nielsen, Mogens Brøndsted. / Dihydroazulene-buckminsterfullerene conjugates. I: Journal of Organic Chemistry. 2012 ; Bind 77, Nr. 20. s. 8922-8932.

Bibtex

@article{b2f35f06862e4809a7e75490b0f54d4e,
title = "Dihydroazulene-buckminsterfullerene conjugates",
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.",
keywords = "Azulenes, Fullerenes, Models, Molecular, Molecular Structure",
author = "Marco Santella and Virginia Mazzanti and Martyn Jevric and Parker, {Christian Richard} and Broman, {S{\o}ren Lindb{\ae}k} and Andrew Bond and Nielsen, {Mogens Br{\o}ndsted}",
year = "2012",
doi = "10.1021/jo301306y",
language = "English",
volume = "77",
pages = "8922--8932",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "20",

}

RIS

TY - JOUR

T1 - Dihydroazulene-buckminsterfullerene conjugates

AU - Santella, Marco

AU - Mazzanti, Virginia

AU - Jevric, Martyn

AU - Parker, Christian Richard

AU - Broman, Søren Lindbæk

AU - Bond, Andrew

AU - Nielsen, Mogens Brøndsted

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.

KW - Azulenes

KW - Fullerenes

KW - Models, Molecular

KW - Molecular Structure

U2 - 10.1021/jo301306y

DO - 10.1021/jo301306y

M3 - Journal article

C2 - 22985481

VL - 77

SP - 8922

EP - 8932

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 20

ER -

ID: 46378654