Resonance-assisted hydrogen bonding induced nucleophilic addition to hamper ESIPT: ratiometric detection of cyanide in aqueous media

Shymaprosad Goswami; Abhishek Manna; Sima Paul; Avijit K. Das; Krishnendu Aich; Prasanta K. Nandi

doi:10.1039/C3CC39256B

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Chemical Communications

Issue 28, 2013

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Resonance-assisted hydrogen bonding induced nucleophilic addition to hamper ESIPT: ratiometric detection of cyanide in aqueous media

Shymaprosad Goswami,*^a Abhishek Manna,^a Sima Paul,^a Avijit K. Das,^a Krishnendu Aich^a and Prasanta K. Nandi^a

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Bengal Engineering and Science University, Shibpur, Howrah 711103, India
E-mail: spgoswamical@yahoo.com ;
Fax: +91-3326682916

Chem. Commun., 2013,49, 2912-2914

DOI: 10.1039/C3CC39256B
Received 28 Dec 2012, Accepted 20 Feb 2013
First published online 21 Feb 2013

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Abstract
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For ratiometric “naked eye” detection of CN⁻, an ESIPT exhibiting benzothiazole receptor (BHI) is designed having one aldehyde group ortho and the other aldehyde para to the OH group respectively. Due to RAHBs, the ortho aldehyde group is highly reactive undergoing nucleophilic cyanide addition selectively, which hampered ESIPT. This is also supported by DFT and TD-DFT calculations.

Abstract from Analytical Abstracts 2013

For ratiometric “naked eye” detection of CN^–, an ESIPT exhibiting benzothiazole receptor (BHI) is designed having one aldehyde group ortho and the other aldehyde para to the OH group respectively. Due to RAHBs, the ortho aldehyde group is highly reactive undergoing nucleophilic cyanide addition selectively, which hampered ESIPT. This is also supported by DFT and TD-DFT calculations.

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Shymaprosad Goswami
Abhishek Manna
Sima Paul
Avijit K. Das
Krishnendu Aich
Prasanta K. Nandi

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Resonance-assisted hydrogen bonding induced nucleophilic addition to hamper ESIPT: ratiometric detection of cyanide in aqueous media

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