Schiff Base Substituent-Triggered Efficient Deboration Reaction and Its Application in Highly Sensitive Hydrogen Peroxide Vapor Detection.
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.
State Key Lab of Transducer Technology, Shanghai Institute of Microsystem and Information Technology, Chinese Academy of Sciences , Changning Road 865, Shanghai 200050, China.
Yanyan
Y
Fu
State Key Lab of Transducer Technology, Shanghai Institute of Microsystem and Information Technology, Chinese Academy of Sciences , Changning Road 865, Shanghai 200050, China.|University of the Chinese Academy of Sciences , Yuquan Road 19, Beijing 100039, China.
Junjun
J
Yao
State Key Lab of Transducer Technology, Shanghai Institute of Microsystem and Information Technology, Chinese Academy of Sciences , Changning Road 865, Shanghai 200050, China.|University of the Chinese Academy of Sciences , Yuquan Road 19, Beijing 100039, China.
Wei
W
Xu
State Key Lab of Transducer Technology, Shanghai Institute of Microsystem and Information Technology, Chinese Academy of Sciences , Changning Road 865, Shanghai 200050, China.|University of the Chinese Academy of Sciences , Yuquan Road 19, Beijing 100039, China.
Tianchi
T
Fan
State Key Lab of Transducer Technology, Shanghai Institute of Microsystem and Information Technology, Chinese Academy of Sciences , Changning Road 865, Shanghai 200050, China.|University of the Chinese Academy of Sciences , Yuquan Road 19, Beijing 100039, China.
Zinuo
Z
Jiao
State Key Lab of Transducer Technology, Shanghai Institute of Microsystem and Information Technology, Chinese Academy of Sciences , Changning Road 865, Shanghai 200050, China.
Qingguo
Q
He
State Key Lab of Transducer Technology, Shanghai Institute of Microsystem and Information Technology, Chinese Academy of Sciences , Changning Road 865, Shanghai 200050, China.
Defeng
D
Zhu
State Key Lab of Transducer Technology, Shanghai Institute of Microsystem and Information Technology, Chinese Academy of Sciences , Changning Road 865, Shanghai 200050, China.
Huimin
H
Cao
State Key Lab of Transducer Technology, Shanghai Institute of Microsystem and Information Technology, Chinese Academy of Sciences , Changning Road 865, Shanghai 200050, China.
Jiangong
J
Cheng
D001895:Boron / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry; D005740:Gases / Q000737:chemistry; D006861:Hydrogen Peroxide / Q000032:analysis*; D007097:Imines / Q000737:chemistry; D057230:Limit of Detection; D010084:Oxidation-Reduction; D011789:Quantum Theory; D012545:Schiff Bases / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
D001897:Boronic Acids; D005456:Fluorescent Dyes; D005740:Gases; D007097:Imines; D012545:Schiff Bases; D006861:Hydrogen Peroxide; D001895:Boron