Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores

Huixin Jiang; Virginia Mazzanti; Christian Richard Parker; Søren Lindbæk Broman; Jens Heide Wallberg; Karol Luspai; Adam Brincko; Henrik Grum Kjærgaard; Anders Kadziola; Peter Rapta; Ole Hammerich; Mogens Brøndsted Nielsen

doi:10.3762/bjoc.11.104

Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores

Huixin Jiang, Virginia Mazzanti, Christian Richard Parker, Søren Lindbæk Broman, Jens Heide Wallberg, Karol Luspai, Adam Brincko, Henrik Grum Kjærgaard, Anders Kadziola, Peter Rapta, Ole Hammerich, Mogens Brøndsted Nielsen

Department of Chemistry

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Abstract

A selection of cyclic and acyclic acetylenic scaffolds bearing two tetrathiafulvalene (TTF) units was prepared by different metal-catalyzed coupling reactions. The bridge separating the two TTF units was systematically changed from linearly conjugated ethyne, butadiyne and tetraethynylethene (trans-substituted) units to a cross-conjugated tetraethynylethene unit, placed in either acyclic or cyclic arrangements. The cyclic structures correspond to so-called radiaannulenes having both endo- and exocyclic double bonds. Interactions between two redox-active TTF units in these molecules were investigated by cyclic voltammetry, UV - vis - NIR and EPR absorption spectroscopical methods of the electrochemically generated oxidized species. The electron-accepting properties of the acetylenic cores were also investigated electrochemically.

Original language	English
Journal	Beilstein Journal of Organic Chemistry
Volume	11
Pages (from-to)	930-948
Number of pages	19
ISSN	2195-951X
DOIs	https://doi.org/10.3762/bjoc.11.104
Publication status	Published - 2 Jun 2015

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Jiang, H., Mazzanti, V., Parker, C. R., Broman, S. L., Wallberg, J. H., Luspai, K., Brincko, A., Kjærgaard, H. G., Kadziola, A., Rapta, P., Hammerich, O., & Nielsen, M. B. (2015). Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores. Beilstein Journal of Organic Chemistry, 11, 930-948. https://doi.org/10.3762/bjoc.11.104

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title = "Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores",

abstract = "A selection of cyclic and acyclic acetylenic scaffolds bearing two tetrathiafulvalene (TTF) units was prepared by different metal-catalyzed coupling reactions. The bridge separating the two TTF units was systematically changed from linearly conjugated ethyne, butadiyne and tetraethynylethene (trans-substituted) units to a cross-conjugated tetraethynylethene unit, placed in either acyclic or cyclic arrangements. The cyclic structures correspond to so-called radiaannulenes having both endo- and exocyclic double bonds. Interactions between two redox-active TTF units in these molecules were investigated by cyclic voltammetry, UV - vis - NIR and EPR absorption spectroscopical methods of the electrochemically generated oxidized species. The electron-accepting properties of the acetylenic cores were also investigated electrochemically.",

author = "Huixin Jiang and Virginia Mazzanti and Parker, {Christian Richard} and Broman, {S{\o}ren Lindb{\ae}k} and Wallberg, {Jens Heide} and Karol Luspai and Adam Brincko and Kj{\ae}rgaard, {Henrik Grum} and Anders Kadziola and Peter Rapta and Ole Hammerich and Nielsen, {Mogens Br{\o}ndsted}",

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T1 - Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores

AU - Jiang, Huixin

AU - Mazzanti, Virginia

AU - Parker, Christian Richard

AU - Broman, Søren Lindbæk

AU - Wallberg, Jens Heide

AU - Luspai, Karol

AU - Brincko, Adam

AU - Kjærgaard, Henrik Grum

AU - Kadziola, Anders

AU - Rapta, Peter

AU - Hammerich, Ole

AU - Nielsen, Mogens Brøndsted

PY - 2015/6/2

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N2 - A selection of cyclic and acyclic acetylenic scaffolds bearing two tetrathiafulvalene (TTF) units was prepared by different metal-catalyzed coupling reactions. The bridge separating the two TTF units was systematically changed from linearly conjugated ethyne, butadiyne and tetraethynylethene (trans-substituted) units to a cross-conjugated tetraethynylethene unit, placed in either acyclic or cyclic arrangements. The cyclic structures correspond to so-called radiaannulenes having both endo- and exocyclic double bonds. Interactions between two redox-active TTF units in these molecules were investigated by cyclic voltammetry, UV - vis - NIR and EPR absorption spectroscopical methods of the electrochemically generated oxidized species. The electron-accepting properties of the acetylenic cores were also investigated electrochemically.

AB - A selection of cyclic and acyclic acetylenic scaffolds bearing two tetrathiafulvalene (TTF) units was prepared by different metal-catalyzed coupling reactions. The bridge separating the two TTF units was systematically changed from linearly conjugated ethyne, butadiyne and tetraethynylethene (trans-substituted) units to a cross-conjugated tetraethynylethene unit, placed in either acyclic or cyclic arrangements. The cyclic structures correspond to so-called radiaannulenes having both endo- and exocyclic double bonds. Interactions between two redox-active TTF units in these molecules were investigated by cyclic voltammetry, UV - vis - NIR and EPR absorption spectroscopical methods of the electrochemically generated oxidized species. The electron-accepting properties of the acetylenic cores were also investigated electrochemically.

U2 - 10.3762/bjoc.11.104

DO - 10.3762/bjoc.11.104

M3 - Journal article

C2 - 26124895

SN - 2195-951X

VL - 11

SP - 930

EP - 948

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores

Abstract

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