Dihydroazulene-buckminsterfullerene conjugates

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 - 2012/10/19

Y1 - 2012/10/19

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

SN - 0022-3263

VL - 77

SP - 8922

EP - 8932

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 20

ER -