Gram-Scale Syntheses and Conductivities of [10]Cycloparaphenylene and Its Tetraalkoxy Derivatives

[10]­Cycloparaphenylene ([10]­CPP) and its tetraalkoxy derivatives were synthesized on the gram scale in 7 steps starting from 1,4-benzoquinone or 2,5-dialkoxy-1,4-benzoquinone. The key steps involve the highly cis-selective bis-addition of 4-bromo-4′-lithiobiphenyl to the quinones to produce a five...

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Veröffentlicht in:Journal of the American Chemical Society 2017-12, Vol.139 (51), p.18480-18483
Hauptverfasser: Kayahara, Eiichi, Sun, Liansheng, Onishi, Hiroaki, Suzuki, Katsuaki, Fukushima, Tatsuya, Sawada, Ayaka, Kaji, Hironori, Yamago, Shigeru
Format: Artikel
Sprache:eng
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Zusammenfassung:[10]­Cycloparaphenylene ([10]­CPP) and its tetraalkoxy derivatives were synthesized on the gram scale in 7 steps starting from 1,4-benzoquinone or 2,5-dialkoxy-1,4-benzoquinone. The key steps involve the highly cis-selective bis-addition of 4-bromo-4′-lithiobiphenyl to the quinones to produce a five-ring unit containing cyclohexa-1,4-diene-3,6-diol moiety, the platinum-mediated dimerization of the five-ring unit, and the H2SnCl4-mediated reductive aromatization of cyclohexadienediol. The tetraalkoxy substituents increased the solubility of [10]­CPP in common organic solvents. The carrier-transport properties of thin films of [10]­CPP and its derivatives were measured for the first time and indicated that [10]­CPP derivatives could rival phenyl-C61-butyric acid methyl ester, which is used widely as an n-type active layer in bulk heterojunction photovoltaics.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b11526