期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 39, 页码 12696-12701出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201806076
关键词
metal-organic frameworks; photodimerization; preorganization; regioselectivity; solid-state organic synthesis
资金
- National Natural Science Foundation of China [21531006, 21701035, 21773163]
- Priority Academic Program Development of Jiangsu Higher Education Institutions
Regioselective photodimerization of trans-4-styrylpyridine (4-spy) derivatives is performed using pseudorotaxane-like Zn-based metal organic frameworks MOFs as templates. The formation of rctt-HT (head-to-tail) dimers is achieved by confining pairs of coordinated 4-spy derivative ligands within hexagonal windows and then irradiating them with UV light. It is also possible to achieve a photodimerization reaction where two different substituted 4-spy ligands are included in such a MOF material. The ether bond formation is employed to protect the sensitive -OH group of HO-spy and the methyl group of CH3O-spy is subsequently removed after the formation of cyclobutane derivative in the CH3O-spy-based MOF. Introducing substituents at the 2- or 3-position of the phenyl group of 4-spy does not significantly affect the rate of the dimerization process except in the case of the strongly electron-withdrawing nitro group where the rate is significantly decreased. These results are in striking contrast to the mixtures of photoproducts and low yields obtained by untemplated photodimerization in organic solvents.
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