Journal
DALTON TRANSACTIONS
Volume 46, Issue 35, Pages 11669-11678Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7dt01158j
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Funding
- Council of Scientific and Industrial Research [01(2694)/12/EMR-II]
- Science and Engineering Research Board [SB/FT/CS-015/2012]
- Board of Research in Nuclear Science [2012/37C/61/BRNS]
- UGC, India
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beta-Dicyanovinyl substituted porphyrinogen (OxP-MN) was synthesized and utilized as a novel multifunctional sensor for the detection of biologically and environmentally important analytes. OxP-MN (1) acts as a selective and reversible probe for rapid colorimetric detection of picric acid (PA) among other nitroaromatics by switching between two porphyrinoid states. This system displayed a higher beta(2) value of 1.7 x 10(8) M-2 and was able to detect PA down to 1.12 ppm (4.99 mu M). beta-Dicyanovinyl substituted porphyrinogen (OxP-MN) reported here contains a porphyrinogen anion binding site and a dicyanovinyl group as a cyanide-dependent reactive subunit. OxP-MN displayed the first evidence that a beta-electron acceptor through a vinyl linker in the case of porphyrinogen results in only an abated shift in the spectrum in contrast to its porphyrin analogues. Porphyrinogen OxP-MN (1) can be switched between a number of porphyrinoid states such as metalloporphodimethene, metalloporphyrin, porphyrinogen, etc. by using CN-, F-and other basic anions. In addition, OxP-MN unveils the unique property of detecting toxic cyanide ions and fluoride ions when hidden within a mixture of other anions. Also, OxP-MN behaves as a dual sensor for picric acid and basic anions such as F-, CN-, OAc-, and H2PO4- via the indicator displacement assay under the unrestricted queue.
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