期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 28, 期 37, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202200978
关键词
dimerization; molecular recognition; post-modification; self-assembly; solid-state reactions
资金
- National Science Foundation [LRM DMR-1708673, CHE-1828117]
This article introduces a method to rapidly diversify the molecules formed in organic crystals by using aryl nitriles as both hydrogen-bond acceptors and modifiable organic groups. The discovery of coexisting supramolecular synthons in the same crystal is also described. The method is demonstrated using a bis(aryl nitrile) alkene that undergoes a hydrogen-bond-directed intermolecular [2+2] photodimerization to form a tetra(aryl nitrile)cyclobutane. The product can be easily converted by click reactivity to a tetra(aryl tetrazole) or by hydrolysis to a tetra(aryl carboxylic acid). The integration of aryl nitriles into solid-state reactions opens up broad avenues for the post-modification of products formed in crystalline solids for rapid diversification.
A method to rapidly diversify the molecules formed in organic crystals is introduced, with aryl nitriles playing a novel dual role as both hydrogen-bond acceptors and modifiable organic groups. The discovery of coexisting supramolecular synthons in the same crystal is also described. The general concept is demonstrated by using a bis(aryl nitrile) alkene that undergoes a hydrogen-bond-directed intermolecular [2+2] photodimerization to form a tetra(aryl nitrile)cyclobutane. The product is readily converted by click reactivity to a tetra(aryl tetrazole) and by hydrolysis to a tetra(aryl carboxylic acid). The integration of aryl nitriles into solid-state reactions opens broad avenues to post-modify products formed in crystalline solids for rapid diversification.
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