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 language | American English |
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Pages (from-to) | 10663-10667 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 53 |
Issue number | 40 |
DOIs | |
State | Published - 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