Hexaaryl-carbo-benzenes revisited: a novel synthetic route, crystallographic data, and prospects of electrochemical behavior

An improved 12-step synthetic route and full characterization of hexaphenyl-carbo-benzene (4, 8%) and the p-bis-3,5-di-tert-butylphenyl homologue (11, 4%), are described. The carbo-benzene reference 4 is now accurately described in the crystal state by X-ray diffraction analysis in the chiral space...

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Published inNew journal of chemistry Vol. 41; no. 10; pp. 3908 - 3914
Main Authors Zhu, Chongwei, Duhayon, Carine, Romero-Borja, Daniel, Maldonado, Jose-Luis, Ramos-Ortiz, Gabriel, Saquet, Alix, Maraval, Valerie, Chauvin, Remi
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2017
Royal Society of Chemistry [1987-....]
Subjects
Chemical Sciences
Chemistry
Chemistry, Multidisciplinary
Coordination chemistry
Physical Sciences
Science & Technology
AROMATICITY
HOMOAROMATICITY
MERS
CHROMOPHORES
RING CARBOMERS
MOLECULES
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Summary:An improved 12-step synthetic route and full characterization of hexaphenyl-carbo-benzene (4, 8%) and the p-bis-3,5-di-tert-butylphenyl homologue (11, 4%), are described. The carbo-benzene reference 4 is now accurately described in the crystal state by X-ray diffraction analysis in the chiral space group P2(1)2(1)2(1), and in comparison to the less symmetric derivative 11 exhibiting a centro-symmetric packing. According to cyclic voltammetry, both hexaaryl-carbo-benzenes 4 and 11 can behave as both reversible potent electron acceptors and standard electron donors, with respective potentials of -0.73 +/- 1 V and +1.17 +/- 2 V/SCE, respectively. Due to their extremely low solubility, solid films of 11 fabricated using the "wet method", with the initial view of studying charge transport properties, were found to display high roughness.
ISSN:1144-0546
1369-9261
DOI:10.1039/c7nj00028f