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Synthesis of 9,10-bis-ketoenaminoanthryl and 9,10-bis-isoxazolylanthryl linked biscalix[4]arenes: atropisomers and molecular recognitions. | LitMetric

AI Article Synopsis

  • A new method was developed for creating biscalix[4]arenes 5-10 using 1,3-dipolar cycloaddition reactions.
  • Biscalix[4]arene 10 can effectively form complexes with methyl viologen due to its suitable cavity size and favorable cation-π interactions.
  • At room temperature, biscalix[4]arenes 8a and 8b exist as atropisomers and cannot exchange conformations due to restricted rotation in certain bonds.

Article 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.

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Source
http://dx.doi.org/10.1021/jo2024784DOI Listing

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