A Tetrameric Cage with D2h Symmetry through Alkyne Metathesis

Hai Long, Qi Wang, Chenxi Zhang, Bruce Noll, Yinghua Jin, Wei Zhang

Research output: Contribution to journalArticlepeer-review

100 Scopus Citations

Abstract

Shape-persistent covalent organic polyhedrons (COPs) with ethynylene linkers are usually prepared through kinetically controlled cross-coupling reactions. The high-yielding synthesis of ethynylene-linked rigid tetrameric cages via one-step alkyne metathesis from readily accessible triyne precursors is presented. The tetrameric cage contains two macrocyclic panels and exhibits D2h symmetry. The assembly of such a COP is a thermodynamically controlled process, which involves the initial formation of macrocycles as key intermediates followed by the connection of two macrocycles with ethynylene linkages. With a large internal cavity, the cage exhibits a high binding selectivity toward C70 (K=3.9×103 Lmol-1) over C60 (no noticeable binding). Clever cages: A tetrameric cage with a D2h symmetry was prepared from a C3-symmetric triyne monomer through a one-step alkyne metathesis. The tetramer consisting of two macrocyclic panels has a large internal cavity, which can selectively host C70 over C60.

Original languageAmerican English
Pages (from-to)10663-10667
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number40
DOIs
StatePublished - 2014

Bibliographical note

Publisher Copyright:
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

NREL Publication Number

  • NREL/JA-2C00-62936

Keywords

  • alkyne metathesis
  • dynamic covalent assembly
  • fullerene receptors
  • organic molecular cages
  • thermodynamic control

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