Schiff Base Substituent-Triggered Efficient Deboration Reaction and Its Application in Highly Sensitive Hydrogen Peroxide Vapor Detection

• Published in: Analytical chemistry (Washington) Vol. 88; no. 10; pp. 5507 - 5512
• Main Authors: Fu, Yanyan, Yao, Junjun, Xu, Wei, Fan, Tianchi, Jiao, Zinuo, He, Qingguo, Zhu, Defeng, Cao, Huimin, Cheng, Jiangong
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 17.05.2016
• Subjects: Analytical chemistry; Borates; Boron; Chemical reactions; Chemical synthesis; Esters; Explosives detection; Fluorescence; Functional groups; Hydrogen peroxide; Imines; Photochemistry; Signatures
• ISSN: 0003-2700; 1520-6882
• DOI: 10.1021/acs.analchem.6b01057

The organic thin-film fluorescence probe, with the advantages of not polluting the analyte and fast response, has attracted much attention in explosive detection. Different with nitro explosives, the peroxide-based explosives are hardly to be detected because of their poor ultraviolet absorption and lack of an aromatic ring. As the signature compound of peroxide-based explosives, H2O2 vapor detection became more and more important. Boron ester or acid is considered to be a suitable functional group for the detection of hydrogen peroxide due to its reliable reactive activity. Its only drawback lies on its slow degradation velocity. In this work, we try to introduce some functional group to make the boron ester to be easily oxidized by H2O2. Herein, 4-(phenyl­(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)­phenyl)­amino)­benzaldehyde (OTB) was synthesized and its imine derivatives, OTBXAs, were easily obtained just by putting OTB films in different primary amines vapors. OTBXAs show fast deboronation velocity in H2O2 vapor compared with OTB. The complete reaction time of (E)-N-phenyl-4-((propylimino)­methyl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)­phenyl)­aniline (OTBPA) was even shortened 40 times with a response time of seconds. The detection limit for H2O2 vapor was as low as 4.1 parts per trillion (ppt). Further study showed that it is a general approach to enhance the sensing performance of borate to hydrogen peroxide (H2O2) vapor by introducing an imine into an aromatic borate molecule via a solid/vapor reaction.