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J Org Chem. 2016 Jul 1;81(13):5649-54. doi: 10.1021/acs.joc.6b01115. Epub 2016 Jun 14.

A Shape-Persistent Cryptand for Capturing Polycyclic Aromatic Hydrocarbons.

Author information

1
Shanghai Advanced Research Institute, Chinese Academy of Science , Shanghai 201210, P. R. China.
2
Medicinal Chemistry, ChemBridge Research Laboratories , San Diego, California 92127, United States.
3
Shanghai Key Laboratory of Green Chemistry and Chemical Processes and Department of Chemistry, East China Normal University , Shanghai 200062, P. R. China.

Abstract

A shape-persistent cryptand 1, containing two face-to-face oriented electron-deficient 2,4,6-triphenyl-1,3,5-triazine units separated by approximately 7 Å, and bridged by two rigid 1,8-naphthyridine linkers and a pentaethylene oxide loop, is created for capturing polycyclic aromatic hydrocarbons. Cryptand 1 formed 1:1 complexes with PAH guest molecules, such as phenanthrene (6), anthracene (7), pyrene (8), triphenylene (9), and tetraphene (10). The single-crystal structure of complex 6⊂1 revealed that 6 was included in the cavity of 1 via face-to-face π···π stacking interactions. Soaking crystalline 1 in a toluene solution of anthracene resulted in anthracene from the toluene solution being picked up by the crystalline solid of 1.

PMID:
27258531
DOI:
10.1021/acs.joc.6b01115

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