Synthesis of elongated cavitands via click reactions and their use as chemosensors

Zsolt Csók, Tímea Kégl, Yin Li, Rita Skoda-Földes, László Kiss, Sándor Kunsági-Máté, Matthew H. Todd, László Kollár

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6 Citations (Scopus)

Abstract

A very efficient modular reaction protocol was developed to attach various functionalities to a rigid cavitand scaffold. In this way, aryl, iodoaryl, benzyl, pyrrolidylmethyl groups, as well as a polyethylene-glycol chain were attached to the 'triazol-level' of the cavitand. The palladium-catalyzed ethynylation of the iodoarene moieties, followed by the copper(I)-catalyzed azide-alkyne cycloaddition produced novel cavitands with significantly elongated binding pockets. The dimensions of these molecules are calculated to be at least 9 Å×18 Å, which place them amongst the largest unimolecular hosts obtained by pure covalent synthesis. A cavitand-based click conjugate is used for selective complexation of Cu2+ and Fe 3+, providing significant fluorescent quenching.

Original languageEnglish
Pages (from-to)8186-8190
Number of pages5
JournalTetrahedron
Volume69
Issue number38
DOIs
Publication statusPublished - Sep 23 2013

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Keywords

  • Azide-alkyne cycloaddition
  • Cavitand
  • Copper
  • Iron
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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