Citation: Kangmin Wang, Liqiu Wan, Jingyu Wang, Chunlin Zhou, Ke Yang, Liang Zhou, Bijin Li. Multifunctional 2-(2′-hydroxyphenyl)benzoxazoles: Ready synthesis, mechanochromism, fluorescence imaging, and OLEDs[J]. Chinese Chemical Letters, ;2024, 35(10): 109554. doi: 10.1016/j.cclet.2024.109554 shu

Multifunctional 2-(2′-hydroxyphenyl)benzoxazoles: Ready synthesis, mechanochromism, fluorescence imaging, and OLEDs

Kangmin Wang ^a ,
Liqiu Wan ^a ,
Jingyu Wang ^c ,
Chunlin Zhou ^a ,
Ke Yang ^{b, *,} ,
Liang Zhou ^{c, *,} ,
Bijin Li ^{a, b, *,}

a.
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, China
b.
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China
c.
State Key Laboratory of Rare Earth Resource Utilization, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China

keyang@cczu.edu.cn

zhoul@ciac.ac.cn

bijinli@cqu.edu.cn

Received Date: 5 October 2023
Revised Date: 10 January 2024
Accepted Date: 19 January 2024
Available Online: 23 January 2024

Figures(6)

Triphenylamine (TPA)-containing 2-(2′-hydroxyphenyl)benzoxazoles (2a-2c) have been synthesized via a highly efficient rhodium-catalyzed C–H/C–H cross-coupling reaction. Compound 2a is a novel mechanofluorochromic material with blue-shifted mechanochromic properties. Compounds 2b and 2c presented opposite mechanochromic trends. For 2b, the enol-form emission enhanced, and the keto-form emission blue-shift after grinding. In contrast, 2c exhibited the weak enol-form emission disappeared and the keto-form emission slightly red-shift after grinding treatments. The estrone-containing 2b-based water-dispersed nanoparticles (NPs) exhibit apparent dual-emission and were applied for fluorescence images. In addition, bis(TPA)-containing 2c-based devices exhibit dual-emission with good performance and a singlet exciton yield of 92%, which breaks through the theoretical upper limit of 25% in conventional fluorescent OLEDs. This is one of the highest exciton utilization values recorded for the ESIPT molecules with a dual emission system.
- Rhodium-catalyzed,
- 2-(2′-Hydroxyphenyl)benzoxazoles,
- Mechanochromism,
- Fluorescence images,
- OLEDs
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