2024-03-28T15:51:52Z
https://soar-ir.repo.nii.ac.jp/oai
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2022-12-14T04:16:28Z
1169:1170
Synthesis, Properties, and Redox Behavior of Tris-(1-azulenyltetracyanobutadiene) and Tris[1-azulenylbis(tetracyanobutadiene)] Chromophores Connected to a 1,3,5-Tri(1-azulenyl)benzene Core
Shoji, Taku
Maruyama, Akifumi
Shimomura, Erika
Nagai, Daichi
Ito, Shunji
Okujima, Tetsuo
Toyota, Kozo
This is the peer reviewed version of the following article: Shoji, T. , Maruyama, A. , Shimomura, E. , Nagai, D. , Ito, S. , Okujima, T. and Toyota, K. (2015), Synthesis, Properties, and Redox Behavior of Tris(1‐azulenyltetracyanobutadiene) and Tris[1‐azulenylbis(tetracyanobutadiene)] Chromophores Connected to a 1,3,5‐Tri(1‐azulenyl)benzene Core. Eur. J. Org. Chem., 2015: 1979-1990. doi:10.1002/ejoc.201403556, which has been published in final form at https://doi.org/10.1002/ejoc.201403556 . This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Redox chemistry
Donor-acceptor systems
Azulenes
Cycloaddition
Chromophores
Tris(1-azulenylacetylene) and tris(1-azulenylethynylarylacetylene) chromophores connected to a 1,3,5-tri(1-azulenyl)benzene core have been prepared by the Pd-catalyzed alkynylations of 1-ethynylazulene with tris(3-iodo-1-azulenyl)benzene or iodoarene derivatives substituted with a 1-azulenylethynyl group with tris(3-ethynyl-1-azulenyl)benzene under Sonogashira-Hagihara cross-coupling conditions. These compounds reacted with tetracyanoethylene in formal [2+2] cycloaddition-retroelectrocyclization reactions to afford the corresponding tris(1-azulenyltetracyanobutadiene) and tris[1-azulenylbis(tetracyanobutadiene)] chromophores in excellent yields. The redox behavior of the tetracyanobutadiene (TCBD) derivatives was examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV), which revealed their multistep electrochemical reduction properties. Moreover, significant color changes were observed by visible spectroscopy under the electrochemical reduction conditions.
Article
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2015(9):1979-1990 (2015)
WILEY-V C H VERLAG GMBH
2015-03
eng
journal article
AM
http://hdl.handle.net/10091/00020646
https://soar-ir.repo.nii.ac.jp/records/19885
https://doi.org/10.1002/ejoc.201403556
10.1002/ejoc.201403556
1434-193X
AA1118165X
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
2015
9
1979
1990
https://soar-ir.repo.nii.ac.jp/record/19885/files/Eur_J_Org_Chem_2015_1979-1990.pdf
application/pdf
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2018-06-13