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

Karsten Stein Jennum; Mikkel Vestergaard; Anders Holmen Pedersen; Jeppe Fock; Jonas Jensen; Marco Santella; Jens Jørgen Led; Kristine Kilså; Thomas Bjørnholm; Mogens Brøndsted Nielsen

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

Karsten Stein Jennum, Mikkel Vestergaard, Anders Holmen Pedersen, Jeppe Fock, Jonas Jensen, Marco Santella, Jens Jørgen Led, Kristine Kilså, Thomas Bjørnholm, Mogens Brøndsted Nielsen

20 Citations (Scopus)

Abstract

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.

Original language	English
Journal	Synthesis
Volume	4
Pages (from-to)	539-548
ISSN	0039-7881
Publication status	Published - 2011

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title = "Synthesis of Oligo(phenyleneethynylene)s with Vertically Disposed Tetrathiafulvalene Units",

abstract = "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.",

author = "Jennum, {Karsten Stein} and Mikkel Vestergaard and Pedersen, {Anders Holmen} and Jeppe Fock and Jonas Jensen and Marco Santella and Led, {Jens J{\o}rgen} and Kristine Kils{\aa} and Thomas Bj{\o}rnholm and Nielsen, {Mogens Br{\o}ndsted}",

year = "2011",

language = "English",

volume = "4",

pages = "539--548",

journal = "Synthesis",

issn = "0039-7881",

publisher = "GeorgThieme Verlag",

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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

JF - Synthesis

ER -

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

Abstract

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