Bis(4-fluorophenyl) substituted oxazole(2,5-Oxz) and C2(5)-C2'(5') linked bioxazole isomers(C2-C2'_BOxz,C2-C5'_BOxz and C5-C5'_BOxz) were concisely synthesized via palladium-catalyzed regioselectiv...Bis(4-fluorophenyl) substituted oxazole(2,5-Oxz) and C2(5)-C2'(5') linked bioxazole isomers(C2-C2'_BOxz,C2-C5'_BOxz and C5-C5'_BOxz) were concisely synthesized via palladium-catalyzed regioselective and sequential C-H arylation in 1-3 reaction steps along with 20%-83% of total yields from oxazole and4-bromofluorobenzene.The linking orientation plays a key role in the packing geometry and photophysical properties of C2-C2'_BOxz,C2-C5'_BOxz and C5-C5'_BOxz.These bioxazole isomers in solid state showed significant differences in photoluminescence quantum yields(PLQY)(0.33,0.25 and 0.04,respectively),delayed fluorescence properties and powder X-ray diffraction(PXRD) patterns,suggesting the divergence in intermolecular interactions.The theoretically calculated gradient isosurfaces and complexation energies indicate the existence of intense π-π interactions between molecular layers,which are in good agreement with the variation trend of optical properties.展开更多
基金This work was supported by the National Natural Science Foundation of China （31471208, 31671195, and 31271370）, the Natural Science Foundation of Hubei Province （2016CFA012）, the Fundamental Research Funds for the Central Universities, Integrated Innovative Team for Major Human Diseases of Tongji Medical College, and the Front Youth Program, Huazhong University of Science and Technology.
基金the financial support from the National Natural Science Foundation of China(Nos.21801028,11704050,61505015)Scientific Research Project of the Education Department of Sichuan Province(No.2018Z099)Project of Science and Technology Department of Sichuan Province(No.2017FZ0085)。
文摘Bis(4-fluorophenyl) substituted oxazole(2,5-Oxz) and C2(5)-C2'(5') linked bioxazole isomers(C2-C2'_BOxz,C2-C5'_BOxz and C5-C5'_BOxz) were concisely synthesized via palladium-catalyzed regioselective and sequential C-H arylation in 1-3 reaction steps along with 20%-83% of total yields from oxazole and4-bromofluorobenzene.The linking orientation plays a key role in the packing geometry and photophysical properties of C2-C2'_BOxz,C2-C5'_BOxz and C5-C5'_BOxz.These bioxazole isomers in solid state showed significant differences in photoluminescence quantum yields(PLQY)(0.33,0.25 and 0.04,respectively),delayed fluorescence properties and powder X-ray diffraction(PXRD) patterns,suggesting the divergence in intermolecular interactions.The theoretically calculated gradient isosurfaces and complexation energies indicate the existence of intense π-π interactions between molecular layers,which are in good agreement with the variation trend of optical properties.
