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- Title
<italic>Carbo</italic>‐biphenyls and <italic>Carbo</italic>‐terphenyls: Oligo(phenylene ethynylene) Ring <italic>Carbo</italic>‐mers.
- Authors
Zhu, Chongwei; Poater, Albert; Duhayon, Carine; Kauffmann, Brice; Saquet, Alix; Maraval, Valérie; Chauvin, Remi
- Abstract
Abstract: Ring <italic>carbo</italic>‐mers of oligo(phenylene ethynylene)s (OPE<italic>n</italic>, <italic>n</italic>=0–2), made of C2‐catenated C18<italic>carbo</italic>‐benzene rings, have been synthesized and characterized by NMR and UV‐vis spectroscopy, crystallography and voltammetry. Analyses of crystal and DFT‐optimized structures show that the C18 rings preserve their individual aromatic character according to structural and magnetic criteria (NICS indices). <italic>Carbo</italic>‐terphenyls (<italic>n</italic>=2) are reversibly reduced at ca. −0.42 V/SCE, i.e. 0.41 V more readily than the corresponding <italic>carbo</italic>‐benzene (−0.83 V/SCE), thus revealing efficient inter‐ring π‐conjugation. An accurate linear fit of <italic>E</italic>1/2red1 vs. the DFT LUMO energy suggests a notably higher value (−0.30 V/SCE) for a <italic>carbo</italic>‐quaterphenyl congener (<italic>n</italic>=3). Increase with <italic>n</italic> of the effective π‐conjugation is also evidenced by a red shift of two of the three main visible light absorption bands, all being assigned to TDDFT‐calculated excited states, one of them restricting to a HOMO→LUMO main one‐electron transition.
- Subjects
ETHER (Anesthetic); DICHLOROMETHANE; SILICA gel; COLUMN chromatography; SPIN-spin coupling constants
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 20, p5742
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201713411