Catechol Moiety Integrated Tri-Aryl Type AIEgen for Visual and Quantitative Boronic Acid Detection

被引:5
作者
Hu, Renjian [1 ]
Lin, Shiyun [2 ]
Wang, Mengshi [1 ]
Li, Ruoxin [1 ]
Shuai, Zhigang [2 ]
Wei, Yen [1 ,3 ,4 ]
机构
[1] Tsinghua Univ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China
[2] Tsinghua Univ, Dept Chem, MOE Key Lab Organ Optoelect & Mol Engn, Beijing 100084, Peoples R China
[3] Chung Yuan Christian Univ, Ctr Nanotechnol, Dept Chem, Chungli 32023, Taiwan
[4] Chung Yuan Christian Univ, Inst Biomed Technol, Chungli 32023, Taiwan
基金
中国国家自然科学基金;
关键词
boronic acid recognition; catechol moiety; dual-mode detection; functional AIEgen; tetra-coordinated boron; AGGREGATION-INDUCED EMISSION; PROTON-TRANSFER; RECEPTORS; SENSORS;
D O I
10.1002/chem.202103351
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Novel functional AIEgen based on three compact bound aryl skeletons is designed and synthesized. This tri-aryl type luminogen (TA-Catechol) embedded with catechol moiety responds rapidly to series of boronic acids. Real-time visual and quantitative dual-mode detection method is established for the first time with modest precision and low detection limit (8.0 mu M). Detailed mechanistic discussion identifies tetra-coordinated boronic species as the key intermediate within sensing procedure. Wide range of organic boronic acids compatible with this strategy is displayed which is promising in high throughput screening technology. Furthermore, solid-state sensing capability of TA-Catechol is also demonstrated.
引用
收藏
页数:9
相关论文
共 57 条
[1]  
[Anonymous], 2017, ANGEW CHEM, V129, P11860
[2]  
[Anonymous], 2011, Angew. Chem, V123, P11132
[3]  
[Anonymous], 1979, LITTLE ACORNS TALL O
[4]  
[Anonymous], 1996, ANGEW CHEM-GER EDIT, V108, P2038
[5]   Detection of Boronic Acids through Excited-State Intramolecular Proton-Transfer Fluorescence [J].
Aronoff, Matthew R. ;
VanVeller, Brett ;
Raines, Ronald T. .
ORGANIC LETTERS, 2013, 15 (20) :5382-5385
[6]   Benchtop monitoring of reaction progress via visual recognition with a handheld UV lamp: In situ monitoring of boronic acids in the Suzuki-Miyaura reaction [J].
Barder, Timothy E. ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2007, 9 (01) :137-139
[7]   EFFECT OF CYCLODEXTRIN COMPLEXATION ON THE PHOTOCHEMISTRY OF XANTHONE - ABSOLUTE MEASUREMENT OF THE KINETICS FOR TRIPLET-STATE EXIT [J].
BARRA, M ;
BOHNE, C ;
SCAIANO, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8075-8079
[8]   Boron delivery agents for neutron capture therapy of cancer [J].
Barth, Rolf F. ;
Mi, Peng ;
Yang, Weilian .
CANCER COMMUNICATIONS, 2018, 38 :1-15
[9]   A SPECTROPHOTOMETRIC INVESTIGATION OF THE INTERACTION OF IODINE WITH AROMATIC HYDROCARBONS [J].
BENESI, HA ;
HILDEBRAND, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (08) :2703-2707
[10]   Comprehensive Chirality Sensing: Development of Stereodynamic Probes with a Dual (Chir)optical Response [J].
Bentley, Keith W. ;
Wolf, Christian .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (14) :6517-6531