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Issue 2, 2015
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Carbo-cyclohexadienes vs. carbo-benzenes: structure and conjugative properties

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Abstract

Ideally Cs-/C2v-symmetric chromophores, constituted by two electro-active groups conjugated through the carbo-mer of the cyclohexa-1,3-diene core, are selectively prepared by the SnCl2-mediated reduction of tailored hexaoxy-[6]pericyclynes: in the latter substrates, one of the 1,4-dioxybut-2-yne edges is “chemically locked” by two CF3 substituents preventing complete reduction to the corresponding aromatic carbo-benzenic core, which is expected to be more “π-insulating” between the electro-active ends. The bis-trifluoromethylated carbo-cyclohexadiene products are also shown to be significantly stabilized with respect to their bis-phenylated analogues. Their structural (crystal X-ray diffraction analyses), spectroscopical (NMR and UV-vis spectra), physio-optical (dichromism in solution) and electrochemical (cyclic voltammograms) properties are compared on the basis of the electron-donating/electron-withdrawing nature of the substituents. These properties are also compared with those of their aromatic carbo-benzene and flexible carbo-n-butadiene counterparts.

Graphical abstract: Carbo-cyclohexadienes vs. carbo-benzenes: structure and conjugative properties

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Publication details

The article was received on 06 Sep 2014, accepted on 04 Nov 2014 and first published on 07 Nov 2014


Article type: Edge Article
DOI: 10.1039/C4SC02742F
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Citation: Chem. Sci., 2015,6, 1139-1149
  • Open access: Creative Commons BY-NC license
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    Carbo-cyclohexadienes vs. carbo-benzenes: structure and conjugative properties

    A. Rives, I. Baglai, C. Barthes, V. Maraval, N. Saffon-Merceron, A. Saquet, Z. Voitenko, Y. Volovenko and R. Chauvin, Chem. Sci., 2015, 6, 1139
    DOI: 10.1039/C4SC02742F

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