Citation: Qiang Guo, Li Tao, Chuanqi Liu, Xiaoyun Zhao, Danyang Wan, Jincheng Zhang, Jianping Ai, Jie Li. Orientation effects on C2(5)-C2'(5') linked bioxazole isomers synthesized via regioselective and sequential C—H arylation[J]. Chinese Chemical Letters, ;2021, 32(1): 425-428. doi: 10.1016/j.cclet.2020.05.010 shu

Orientation effects on C2(5)-C2'(5') linked bioxazole isomers synthesized via regioselective and sequential C—H arylation

Qiang Guo ^a ,
Li Tao ^a ,
Chuanqi Liu ^a ,
Xiaoyun Zhao ^a ,
Danyang Wan ^b ,
Jincheng Zhang ^a ,
Jianping Ai ^a ,
Jie Li ^{a, c, *,}

a.
College of Optoelectronic Engineering, Chengdu University of Information Technology, Chengdu 610225, China
b.
Optical and Electrical Material Center, Xi'an Modern Chemistry Research Institute, Xi'an 710065, China
c.
National Engineering Research Center for Domestic and Building Ceramics, Jingdezhen Ceramic Institute, Jingdezhen 333403, China

lijie@cuit.edu.cn

Received Date: 5 April 2020
Revised Date: 29 April 2020
Accepted Date: 9 May 2020
Available Online: 19 May 2020

Figures(3)

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 and 4-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.
- Bioxazole isomers,
- Palladium-catalyzed,
- C—H arylation,
- Orientation effects,
- Photophysical properties,
- Theoretical calculation
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