Synthesis of 9,10-bis-ketoenaminoanthryl and 9,10-bis-isoxazolylanthryl linked biscalix[4]arenes: Atropisomers and molecular recognitions

Chia Chen Tsai, I. Ting Ho, Jean Ho Chu, Li Ching Shen, Shou Ling Huang, Wen-Sheng Chung*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

An efficient synthetic pathway for the synthesis of biscalix[4]arenes 5-10 using 1,3-dipolar cycloaddition reactions is reported. Biscalix[4]arene 10 is capable of forming a complex with methyl viologen because of favorable cation-π interactions and a proper cavity size to accommodate the guest. Moreover, biscalix[4]arenes 8a and 8b were found to be atropisomers at room temperature. These two conformers were unable to exchange at room temperature because of the restricted rotation of the C 9-C 11 or C 10-C 12 bonds of the β-amino-α,β- unsaturated ketones of anthracene.

Original languageEnglish
Pages (from-to)2254-2262
Number of pages9
JournalJournal of Organic Chemistry
Volume77
Issue number5
DOIs
StatePublished - 2 Mar 2012

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