Calix[4]arene-click-cyclodextrin and supramolecular structures with watersoluble NIPAAM-copolymers bearing adamantyl units: "Rings on ring on chain"

Bernd Garska; Monir Tabatabai; Helmut Ritter

doi:10.3762/bjoc.6.83

Calix[4]arene-click-cyclodextrin and supramolecular structures with watersoluble NIPAAM-copolymers bearing adamantyl units: "Rings on ring on chain"

Beilstein J Org Chem. 2010 Aug 5:6:784-8. doi: 10.3762/bjoc.6.83.

Authors

Bernd Garska¹, Monir Tabatabai, Helmut Ritter

Affiliation

¹ Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225 Düsseldorf, Germany. bernd.garska@uni-duesseldorf.de

Abstract

We describe the calixarene-cyclodextrin-coupling via click reaction starting from 5,11,17,23-tetra-tert-butyl-25,27-dipropargylether-26,28-hydroxy-calix[4]arene (calix[4]arene-dipropargylether) (2) onto 6I-azido-6I-deoxycyclomaltoheptaose (3) under microwave assisted conditions. The coupling was proven by MALDI-TOF mass spectrometry, ¹H NMR and IR-spectroscopy. The pH dependent supramolecular complex formation with poly(NIPAAM) bearing attached adamantyl units was investigated by dynamic light scattering (DLS) and turbidity measurements.

Keywords: calix[4]arene; click chemistry; poly(NIPAAM); β-cyclodextrin.