期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 31, 页码 13133-13140出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja3058502
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资金
- National Science Foundation [CHE-1110911]
- National Institutes of Health [GM021248]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1110911] Funding Source: National Science Foundation
We present a building-block approach toward functionalized CB[7] derivatives by the condensation of methylene-bridged glycoluril hexamer 1 and glycoluril bis(cyclic ethers) 2 and 12. The CB[7] derivatives Me2CB[7] and CyCB[7] are highly soluble in water (264 mM and 181 mM, respectively). As a result of the high intrinsic solubility of Me2CB[7], it is able to solubilize the insoluble benzimidazole drug albendazole. The reaction of hexamer 1 with glycoluril derivative 12, which bears a primary alkyl chloride group, gives CB[7] derivative 18 in 16% isolated yield. Compound 18 reacts with NaN3 to yield azide-substituted CB[7] 19 in 81% yield, which subsequently undergoes click reaction with propargylammonium chloride (21) to yield CB[7] derivative 20 in 95% yield, which bears a covalently attached triazolyl ammonium group along its equator. The results of NMR spectroscopy (H-1, variable-temperature, and DOSY) and electrospray mass spectrometry establish that 20 undergoes self-assembly to form a cyclic tetrameric assembly (20(4)) in aqueous solution. CB[7] derivatives bearing reactive functional groups (e.g., N-3, Cl) are now available for incorporation into more complex functional systems.
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