3,5-Diformylboron Dipyrromethenes as Fluorescent pH Sensors
DSpace at IIT Bombay
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Title |
3,5-Diformylboron Dipyrromethenes as Fluorescent pH Sensors
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Creator |
MADHU, S
RAO, MR SHAIKH, MS RAVIKANTH, M |
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Subject |
QUANTUM-CHEMICAL CALCULATIONS
NEAR-INFRARED NIR BODIPY DYES SPECTROSCOPIC PROPERTIES SPECTRAL PROPERTIES CRYSTAL-STRUCTURE BORON PHOTOPHYSICS ELECTROCHEMISTRY FLUOROIONOPHORE |
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Description |
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.
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Publisher |
AMER CHEMICAL SOC
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Date |
2012-06-26T08:49:13Z
2012-06-26T08:49:13Z 2011 |
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Type |
Article
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Identifier |
INORGANIC CHEMISTRY,50(10)4392-4400
0020-1669 http://dx.doi.org/10.1021/ic102499h http://dspace.library.iitb.ac.in/jspui/handle/100/14223 |
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Language |
English
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