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Boron-Dipyrromethene Based Reversible and Reusable Selective Chemosensor for Fluoride Detection

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Title Boron-Dipyrromethene Based Reversible and Reusable Selective Chemosensor for Fluoride Detection
 
Creator MADHU, S
RAVIKANTH, M
 
Subject TRANSFER SIGNALING MECHANISM
PROTON-TRANSFER
FLUORESCENT CHEMOSENSOR
ANION-BINDING
LIVING CELLS
BODIPY DYES
SPECTROSCOPIC PROPERTIES
ION
SENSOR
RECEPTOR
 
Description We synthesized benzimidazole substituted boron-dipyrromethene 1 (BODIPY 1) by treating 3,5-diformyl BODIPY 2 with o-phenylenediamine under mild acid catalyzed conditions and characterized by using various spectroscopic techniques. The X-ray structure analysis revealed that the benzimidazole NH group is involved in intramolecular hydrogen bonding with fluoride atoms which resulted in a coplanar geometry between BODIPY and benzimidazole moiety. The presence of benzimidazole moiety at 3-position of BODIPY siginificantly altered the electronic properties, which is clearly evident in bathochromic shifts of absorption and fluorescence bands, improved quantum yields, increased lifetimes compared to BODIPY 2. The anion binding studies indicated that BODIPY 1 showed remarkable selectivity and specificity toward F- ion over other anions. Addition of F- ion to BODIPY 1 resulted in quenching of fluorescence accompanied by a visual detectable color change from fluorescent pink to nonfluorescent blue.. The recognition mechanism is attributed to a fluoride-triggered disruption of the hydrogen bonding between BODIPY and benzimidazole moieties leading to (i) noncoplanar geometry between BODIPY and benzimidazole units and (ii) operation of photoinduced electron transfer (PET) from benzimidazole moiety to BODIPY unit causing quenching of fluorescence. Interestingly, when we titrated the nonfluorescent blue 1-F- solution with TFA resulted in a significant enhancement of fluorescence intensity (15-fold) because the PET quenching is prevented due to protonation of benzimidazole group. Furthermore, the reversibility and reusability of sensor 1 for the detection of F- ion was tested for six cycles indicating the sensor 1 is stable and can be used in reversible manner.
 
Publisher AMER CHEMICAL SOC
 
Date 2014-12-28T12:26:05Z
2014-12-28T12:26:05Z
2014
 
Type Article
 
Identifier INORGANIC CHEMISTRY, 53(3)1646-1653
0020-1669
1520-510X
http://dx.doi.org/10.1021/ic402767j
http://dspace.library.iitb.ac.in/jspui/handle/100/16514
 
Language English