Synthesis and photo-property of 2-cyano boron-dipyrromethene and the application for detecting fluoride ion
Three 2-cyano boron-dipyrromethene (BODIPY) based derivatives (CB1–CB3) have been synthesized and characterized. The photophysical properties of these compounds are investigated by means of UV/Vis absorption and fluorescence spectroscopy. CB1–CB3 exhibit small Stokes shift and high fluorescence quan...
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| Published in | Tetrahedron Vol. 71; no. 52; pp. 9611 - 9616 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier Ltd
30.12.2015
Elsevier |
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| Abstract | Three 2-cyano boron-dipyrromethene (BODIPY) based derivatives (CB1–CB3) have been synthesized and characterized. The photophysical properties of these compounds are investigated by means of UV/Vis absorption and fluorescence spectroscopy. CB1–CB3 exhibit small Stokes shift and high fluorescence quantum yield. Noticeably, CB2 with styrene moieties at 5-position of BODIPY displays absorption alternation with maximum of 120 nm red-shift upon addition of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) as a base, giving remarkable color change which can be detected by naked eye. Meanwhile, the compound CB3 shows high selectivity toward fluoride ion via fluorescence quenching mechanism by release of the masked phenolate form of CB2 through fluoride ion induced deprotection reaction. It also exhibits fast signal response time (30 s) and excellent selectivity over other competing analytes, making it a good candidate as colorimetric sensor for fluoride sensing.
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| AbstractList | Three 2-cyano boron-dipyrromethene (BODIPY) based derivatives (CB1–CB3) have been synthesized and characterized. The photophysical properties of these compounds are investigated by means of UV/Vis absorption and fluorescence spectroscopy. CB1–CB3 exhibit small Stokes shift and high fluorescence quantum yield. Noticeably, CB2 with styrene moieties at 5-position of BODIPY displays absorption alternation with maximum of 120 nm red-shift upon addition of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) as a base, giving remarkable color change which can be detected by naked eye. Meanwhile, the compound CB3 shows high selectivity toward fluoride ion via fluorescence quenching mechanism by release of the masked phenolate form of CB2 through fluoride ion induced deprotection reaction. It also exhibits fast signal response time (30 s) and excellent selectivity over other competing analytes, making it a good candidate as colorimetric sensor for fluoride sensing.
[Display omitted] Three 2-cyano boron-dipyrromethene (BODIPY) based derivatives (CBI-CB3) have been synthesized and characterized. The photophysical properties of these compounds are investigated by means of UV/Vis absorption and fluorescence spectroscopy. CBI-CB3 exhibit small Stokes shift and high fluorescence quantum yield. Noticeably, CB2 with styrene moieties at 5-position of BODIPY displays absorption alternation with maximum of 120 nm red-shift upon addition of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) as a base, giving remarkable color change which can be detected by naked eye. Meanwhile, the compound CB3 shows high selectivity toward fluoride ion via fluorescence quenching mechanism by release of the masked phenolate form of CB2 through fluoride ion induced deprotection reaction. It also exhibits fast signal response time (30 s) and excellent selectivity over other competing analytes, making it a good candidate as colorimetric sensor for fluoride sensing. (C) 2015 Elsevier Ltd. All rights reserved. |
| Author | Wu, Qingqing Dai, Fengyuan Zong, Qianshou Wang, Jianbo Shen, Jinjin Wu, Chenjun |
| Author_xml | – sequence: 1 givenname: Jianbo surname: Wang fullname: Wang, Jianbo email: wjb4207@mail.ustc.edu.cn organization: College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, China – sequence: 2 givenname: Qianshou surname: Zong fullname: Zong, Qianshou organization: College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, China – sequence: 3 givenname: Qingqing surname: Wu fullname: Wu, Qingqing organization: Jiangsu Nhwa Pharmaceutical Co., Ltd, Xuzhou 221000, China – sequence: 4 givenname: Jinjin surname: Shen fullname: Shen, Jinjin organization: College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, China – sequence: 5 givenname: Fengyuan surname: Dai fullname: Dai, Fengyuan organization: College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, China – sequence: 6 givenname: Chenjun surname: Wu fullname: Wu, Chenjun organization: College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, China |
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| Keywords | Bodipy derivatives High selectivity Fluoride ion Colorimetric sensor BODIPY DYES REAGENTS CHEMOSENSORS FLUORESCENCE CHEMISTRY RECEPTORS DERIVATIVES |
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| Snippet | Three 2-cyano boron-dipyrromethene (BODIPY) based derivatives (CB1–CB3) have been synthesized and characterized. The photophysical properties of these... Three 2-cyano boron-dipyrromethene (BODIPY) based derivatives (CBI-CB3) have been synthesized and characterized. The photophysical properties of these... |
| Source | Web of Science |
| SourceID | crossref webofscience elsevier |
| SourceType | Aggregation Database Enrichment Source Index Database Publisher |
| StartPage | 9611 |
| SubjectTerms | Bodipy derivatives Chemistry Chemistry, Organic Colorimetric sensor Fluoride ion High selectivity Physical Sciences Science & Technology |
| Title | Synthesis and photo-property of 2-cyano boron-dipyrromethene and the application for detecting fluoride ion |
| URI | https://dx.doi.org/10.1016/j.tet.2015.10.081 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000366535800004 |
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