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Preparation of a cyclic polyphenylene array for a zigzag-type carbon nanotube segment

, : Preparation of a cyclic polyphenylene array for a zigzag-type carbon nanotube segment. Journal of Organic Chemistry 80(10): 5092-5110

Preparation of cyclic polyphenylene array 2, which corresponds to a complete carbon array of a zigzag-type CNT segment with (18,0)-structure, has been established by a Diels-Alder reaction of cyclic biphenylylene-acetylene derivative 1 with tetraphenylcyclopentadienone. The reaction of 2 with excess FeCl3 realized a presumed cyclodehydrogenation reaction and elimination of the alkyl chains that were introduced as a measure to counter the low solubility problem, but this resulted in the formation of a complicated mixture that included the mass region of a presumed zigzag-type CNT segment with (18,0)-structure. The rather efficient blue emission of cyclic compounds 1 and 2 was discussed utilizing fluorescence (FL) quantum efficiencies (Φ(FL)) and lifetimes (τ(FL)) in their crystalline state along with those in dichloromethane solution. Thermal analyses of these compounds revealed their characteristic phase transition behavior. The synthesis of a novel cyclic polyphenylene array by utilizing a Diels-Alder reaction of cyclic phenylene-acetylene compounds with tetraphenylcyclopentadienone should afford an attractive pathway to a novel belt-shaped CNT segment.


PMID: 25897836

DOI: 10.1021/acs.joc.5b00485

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