Synthesis and structural characterization of a new chiral macrocycle derived from α,α′-(bistrifluoromethyl)-9,10-anthracendimethanol and terephthalic acid

Martina Palomino-Schätzlein, Kepa K. Burusco, Teodor Parella, Albert Virgili, Carlos Jaime

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1 Citation (Scopus)

Abstract

The synthesis and the structural properties of a chiral macrocyclic cyclooctatetracontaphane host are reported. The macrocycle is obtained by cyclization of six molecules of terephthalic acid and six molecules of enantiopure α,α′-(bistrifluoromethyl)-9,10-anthracendimethanol. The later is known for its enantioselective interaction with different organic molecules and is used as effective chiral solvating agent for pharmaceutic mixtures. Experimental NMR diffusion data of the chiral macrocycle reveal a predominant conformation in solution with a cavity, suitable for host-guest interactions. This result is confirmed by theoretical calculations using molecular dynamics. © Springer Science+Business Media B.V. 2009.
Original languageEnglish
Pages (from-to)419-426
JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
Volume65
DOIs
Publication statusPublished - 1 Nov 2009

Keywords

  • Aromatic
  • Diffusion
  • Enantiorecognition
  • Molecular dynamics

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