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Org Lett. 2016 Jul 1;18(13):3126-9. doi: 10.1021/acs.orglett.6b01330. Epub 2016 Jun 21.

Functionalized O6-Corona[6]arenes: Synthesis, Structure, and Fullerene Complexation Property.

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1
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University , Beijing 100084, China.

Abstract

The synthesis, structure, and fullerene complexation property of novel and functionalized On-corona[n]arenes were reported. Based on the fragment coupling strategy, ester-containing On-corona[n]arenes (n = 6, 8) were obtained readily starting from 1,4-hydroquinone and diethyl 2,5-difluoroterephthalate. Reduction of esters with LiAlH4 produced almost quantitatively hydroxymethylated On-corona[n]arenes, which underwent etherification with MeI to afford methoxymethyl-substituted On-corona[n]arenes (n = 6, 8) in good yields. The macrocycles adopt unique corona-type conformation with a large cylindroid cavity. They are strong macrocyclic host molecules to form 1:1 complexes with fullerenes C60 and C70 in toluene with an associate constant up to (1.59 ± 0.04) × 10(5) M(-1).

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