Synthesis of Oligo(phenyleneethynylene)s with Vertically Disposed Tetrathiafulvalene Units

TY - JOUR

T1 - Synthesis of Oligo(phenyleneethynylene)s with Vertically Disposed Tetrathiafulvalene Units

AU - Jennum, Karsten Stein

AU - Vestergaard, Mikkel

AU - Pedersen, Anders Holmen

AU - Fock, Jeppe

AU - Jensen, Jonas

AU - Santella, Marco

AU - Led, Jens Jørgen

AU - Kilså, Kristine

AU - Bjørnholm, Thomas

AU - Nielsen, Mogens Brøndsted

PY - 2011

Y1 - 2011

N2 - Functionalized oligo(phenyleneethynylene)s (OPEs) show potential as molecular wires for molecular electronics. A selection of OPEs with vertically disposed extended tetrathiafulvalene (TTF) units has been synthesized by a combination of metal-catalyzed cross-coupling and Wittig reactions. Two general synthetic routes were developed. In one route, the OPE scaffold was first constructed and finally the extended TTF units were incorporated by Wittig reactions. In the second route, the extended TTF module was first prepared and subsequently incorporated into an OPE backbone by palladium-catalyzed cross-coupling reactions. The latter route was employed for functionalization with protected thiol end-groups. Owing to the shape of these redox-active molecules, they are termed OPE-TTF cruciforms'. The electronic properties were investigated by UV-Vis spectroscopy and by cyclic voltammetry.

AB - Functionalized oligo(phenyleneethynylene)s (OPEs) show potential as molecular wires for molecular electronics. A selection of OPEs with vertically disposed extended tetrathiafulvalene (TTF) units has been synthesized by a combination of metal-catalyzed cross-coupling and Wittig reactions. Two general synthetic routes were developed. In one route, the OPE scaffold was first constructed and finally the extended TTF units were incorporated by Wittig reactions. In the second route, the extended TTF module was first prepared and subsequently incorporated into an OPE backbone by palladium-catalyzed cross-coupling reactions. The latter route was employed for functionalization with protected thiol end-groups. Owing to the shape of these redox-active molecules, they are termed OPE-TTF cruciforms'. The electronic properties were investigated by UV-Vis spectroscopy and by cyclic voltammetry.

M3 - Journal article

SN - 0039-7881

VL - 4

SP - 539

EP - 548

JO - Synthesis (Germany)

JF - Synthesis (Germany)

ER -