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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/100/14223

Title: 3,5-Diformylboron Dipyrromethenes as Fluorescent pH Sensors
Authors: MADHU, S
RAO, MR
SHAIKH, MS
RAVIKANTH, M
Keywords: QUANTUM-CHEMICAL CALCULATIONS
NEAR-INFRARED NIR
BODIPY DYES
SPECTROSCOPIC PROPERTIES
SPECTRAL PROPERTIES
CRYSTAL-STRUCTURE
BORON
PHOTOPHYSICS
ELECTROCHEMISTRY
FLUOROIONOPHORE
Issue Date: 2011
Publisher: AMER CHEMICAL SOC
Citation: INORGANIC CHEMISTRY,50(10)4392-4400
Abstract: A series of boron dipyrromethene (BODIPY) dyes containing two aldehyde functional groups at the 3 and 5 positions have been synthesized in low-to-decent yields in two steps. In the first step, the meso-aryl dipyrromethanes were treated with POCl(3) in N,N-dimethylformamide to afford 1,9-diformylated dipyrromethanes. In the second step, the diformylated dipyrromethanes were first in situ oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and then reacted with BF(3)center dot OEt(2) to afford 3,5-diformylboron dipyrromethenes. The X-ray structural analysis indicated that the aldehyde groups are involved in intramolecular hydrogen bonding with fluoride atoms, which may be responsible for the stability of the diformylated BODIPY compounds. The presence of two formyl groups significantly alters the electronic properties, which is clearly evident in downfield shifts in the (1)H and (19)F NMR spectra, bathochromic shifts in the absorption and fluorescence spectra, better quantum yields, and increased lifetimes compared to 3,5-unsubstituted BODIPYs. Furthermore, 3,5-diformylboron dipyrromethenes are highly electron-deficient and undergo facile reductions compared to unsubstituted BODIPYs. These compounds exhibit pH-dependent on/off fluorescence and thus act as fluorescent pH sensors.
URI: http://dx.doi.org/10.1021/ic102499h
http://dspace.library.iitb.ac.in/jspui/handle/100/14223
ISSN: 0020-1669
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