Complexation Between (O-Methyl)6 -2,6-Helic[6]arene and Tertiary Ammonium Salts: Acid/Base- or Chloride-Ion-Responsive Host-Guest Systems and Synthesis of [2]Rotaxane

Qiang Shi; Ying Han; Chuan-Feng Chen

doi:10.1002/asia.201700857

Complexation Between (O-Methyl)₆ -2,6-Helic[6]arene and Tertiary Ammonium Salts: Acid/Base- or Chloride-Ion-Responsive Host-Guest Systems and Synthesis of [2]Rotaxane

Chem Asian J. 2017 Oct 5;12(19):2576-2582. doi: 10.1002/asia.201700857. Epub 2017 Aug 16.

Authors

Qiang Shi^{1

2}, Ying Han¹, Chuan-Feng Chen^{1

2}

Affiliations

¹ Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
² University of Chinese Academy of Sciences, Beijing, 100049, China.

PMID: 28703463
DOI: 10.1002/asia.201700857

Abstract

Complexation between (O-methyl)₆ -2,6-helic[6]arene and a series of tertiary ammonium salts was described. It was found that the macrocycle could form stable complexes with the tested aromatic and aliphatic tertiary ammonium salts, which were evidenced by ¹ H NMR spectra, ESI mass spectra, and DFT calculations. In particular, the binding and release process of the guests in the complexes could be efficiently controlled by acid/base or chloride ions, which represents the first acid/base- and chloride-ion-responsive host-guest systems based on macrocyclic arenes and protonated tertiary ammonium salts. Moreover, the first 2,6-helic[6]arene-based [2]rotaxane was also synthesized from the condensation between the host-guest complex and isocyanate.

Keywords: ammonium; complexation; host-guest systems; macrocycles; rotaxanes.