期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 40, 页码 10663-10667出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201404880
关键词
alkyne metathesis; dynamic covalent assembly; fullerene receptors; organic molecular cages; thermodynamic control
资金
- National Science Foundation [DMR-1055705]
- Alfred P. Sloan Foundation
- Office of Energy Efficiency and Renewable Energy of the U.S. Department of Energy [DE-AC36-08GO28308]
- Division Of Materials Research
- Direct For Mathematical & Physical Scien [1055705] Funding Source: National Science Foundation
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 D-2h 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 C-70 (K = 3.9 x 10(3) Lmol(-1)) over C-60 (no noticeable binding).
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