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Cross-Conjugated Systems Based On An (E)-Hexa-3-en-1,5-diyne-3,4-diyl Skeleton: Spectroscopic and Spectroelectrochemical Investigations

Gluyas, J.B.G.; Manici, V.; Gückel, S.; Vincent, K.B.; Yufit, D.S.; Howard, J.A.K.; Skelton, B.W.; Beeby, A.; Kaupp, M.; Low, P.J.

Cross-Conjugated Systems Based On An (E)-Hexa-3-en-1,5-diyne-3,4-diyl Skeleton: Spectroscopic and Spectroelectrochemical Investigations Thumbnail


Authors

J.B.G. Gluyas

V. Manici

S. Gückel

K.B. Vincent

D.S. Yufit

J.A.K. Howard

B.W. Skelton

M. Kaupp

P.J. Low



Abstract

A series of cross-conjugated compounds based on an (E)-4,4′-(hexa-3-en-1,5-diyne-3,4-diyl)bis(N,N-bis(4-methoxyphenyl)aniline) skeleton (1–6) have been synthesized. The linear optical absorption properties can be tuned by modification of the substituents at the 1 and 5 positions of the hexa-3-en-1,5-diynyl backbone (1: Si(CH(CH3)2)3, 2: C6H4C≡CSi(CH3)3, 3: C6H4COOCH3, 4: C6H4CF3, 5: C6H4C≡N, 6: C6H4C≡CC5H4N), although attempts to introduce electron-donating (C6H4CH3, C6H4OCH3, C6H4Si(CH3)3) substituents at these positions were hampered by the ensuing decreased stability of the compounds. Spectroelectrochemical investigations of selected examples, supported by DFT-based computational studies, have shown that one- and two-electron oxidation of the 1,2-bis(triarylamine)ethene fragment also results in electronic changes to the perpendicular π-system in the hexa-3-en-1,5-diynyl branch of the molecule. These properties suggest that (E)-hexa-3-en-1,5-diynyl-based compounds could have applications in molecular sensing and molecular electronics.

Citation

Gluyas, J., Manici, V., Gückel, S., Vincent, K., Yufit, D., Howard, J., …Low, P. (2015). Cross-Conjugated Systems Based On An (E)-Hexa-3-en-1,5-diyne-3,4-diyl Skeleton: Spectroscopic and Spectroelectrochemical Investigations. Journal of Organic Chemistry, 80(22), 11501-11512. https://doi.org/10.1021/acs.joc.5b02240

Journal Article Type Article
Online Publication Date Oct 23, 2015
Publication Date Nov 20, 2015
Deposit Date Apr 14, 2016
Publicly Available Date Mar 29, 2024
Journal Journal of Organic Chemistry
Print ISSN 0022-3263
Electronic ISSN 1520-6904
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 80
Issue 22
Pages 11501-11512
DOI https://doi.org/10.1021/acs.joc.5b02240

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Accepted Journal Article (971 Kb)
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Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/acs.joc.5b02240





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