Redox-dependent conformational switching of diphenylacetylenes

Ian M. Jones; Peter C. Knipe; Thoe Michaelos; Sam Thompson; Andrew D. Hamilton

doi:10.3390/molecules190811316

Redox-dependent conformational switching of diphenylacetylenes

Ian M. Jones, Peter C. Knipe, Thoe Michaelos, Sam Thompson, Andrew D. Hamilton

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Herein we describe the design and synthesis of a redox-dependent single-molecule switch. Appending a ferrocene unit to a diphenylacetylene scaffold gives a redox-sensitive handle, which undergoes reversible one-electron oxidation, as demonstrated by cyclic voltammetry analysis. ¹H-NMR spectroscopy of the partially oxidized switch and control compounds suggests that oxidation to the ferrocenium cation induces a change in hydrogen bonding interactions that results in a conformational switch.

Original language	English (US)
Pages (from-to)	11316-11332
Number of pages	17
Journal	Molecules
Volume	19
Issue number	8
DOIs	https://doi.org/10.3390/molecules190811316
State	Published - Aug 2014

Keywords

Amide bond
Ferrocene
Hydrogen bonding
Molecular switch
Redox
Translational isomerism

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

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10.3390/molecules190811316

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abstract = "Herein we describe the design and synthesis of a redox-dependent single-molecule switch. Appending a ferrocene unit to a diphenylacetylene scaffold gives a redox-sensitive handle, which undergoes reversible one-electron oxidation, as demonstrated by cyclic voltammetry analysis. 1H-NMR spectroscopy of the partially oxidized switch and control compounds suggests that oxidation to the ferrocenium cation induces a change in hydrogen bonding interactions that results in a conformational switch.",

keywords = "Amide bond, Ferrocene, Hydrogen bonding, Molecular switch, Redox, Translational isomerism",

author = "Jones, {Ian M.} and Knipe, {Peter C.} and Thoe Michaelos and Sam Thompson and Hamilton, {Andrew D.}",

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AU - Jones, Ian M.

AU - Knipe, Peter C.

AU - Michaelos, Thoe

AU - Thompson, Sam

AU - Hamilton, Andrew D.

PY - 2014/8

Y1 - 2014/8

N2 - Herein we describe the design and synthesis of a redox-dependent single-molecule switch. Appending a ferrocene unit to a diphenylacetylene scaffold gives a redox-sensitive handle, which undergoes reversible one-electron oxidation, as demonstrated by cyclic voltammetry analysis. 1H-NMR spectroscopy of the partially oxidized switch and control compounds suggests that oxidation to the ferrocenium cation induces a change in hydrogen bonding interactions that results in a conformational switch.

AB - Herein we describe the design and synthesis of a redox-dependent single-molecule switch. Appending a ferrocene unit to a diphenylacetylene scaffold gives a redox-sensitive handle, which undergoes reversible one-electron oxidation, as demonstrated by cyclic voltammetry analysis. 1H-NMR spectroscopy of the partially oxidized switch and control compounds suggests that oxidation to the ferrocenium cation induces a change in hydrogen bonding interactions that results in a conformational switch.

KW - Amide bond

KW - Ferrocene

KW - Hydrogen bonding

KW - Molecular switch

KW - Redox

KW - Translational isomerism

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UR - http://www.scopus.com/inward/citedby.url?scp=84906662012&partnerID=8YFLogxK

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SP - 11316

EP - 11332

JO - Molecules

JF - Molecules

IS - 8

ER -

Redox-dependent conformational switching of diphenylacetylenes

Abstract

Keywords

ASJC Scopus subject areas

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