Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 26, Pages 7525-7529Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201601907
Keywords
arynes; fluorine; heterocycles; phosphorus; radicals
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan [23655173, 25109518, 25288033, 15H00923]
- Institute for Chemical Research, Kyoto University [2014-09, 2015-23]
- Nissan Chemicals Co. Ltd.
- Grants-in-Aid for Scientific Research [25288033, 23655173, 25109518, 15H00923] Funding Source: KAKEN
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Tuning of the physicochemical properties of the 1,3-diphosphacyclobutane-2,4-diyl unit is attractive in view of materials applications. The use of arynes is shown to be effective for installing relatively electron rich aryl substituents into the open-shell singlet P-heterocyclic system. Treatment of the sterically encumbered 1,3-diphosphacyclobuten-4-yl anion with ortho-silylated aryl triflates in the presence of fluoride under appropriate conditions afforded the corresponding 1-aryl 1,3-diphosphacyclobutane-2,4-diyls. The air-stable open-shell singlet P-heterocycles exhibit considerable electron-donating character, and the aromatic substituent influences the open-shell character, which is thought to be related to the property of p-type semiconductivity. The P-arylated 1,3-diphosphacyclobutane-2,4-diyl systems can be further utilized as detectors of hydrogen fluoride (HF), which causes a remarkable change in their photoabsorption properties.
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