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Selective recognition of cyanide ions by amphiphilic porphyrins in aqueous medium

Photosciences and Photonics, Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram 695019, Kerala, India

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Suneesh C. Karunakaran

Photosciences and Photonics, Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram 695019, Kerala, India

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Dhanya T. Jayaram

Photosciences and Photonics, Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram 695019, Kerala, India

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Nagappanpillai Adarsh

Photosciences and Photonics, Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram 695019, Kerala, India

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Joshy Joseph

Photosciences and Photonics, Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram 695019, Kerala, India

Academy of Scientific and Innovative Research (AcSIR), CSIR-NIIST Campus, India

E-mail Address: rama@rrljorhat.res

E-mail Address: d.ramaiah@gmail.com

Correspondence to: Danaboyina Ramaiah, tel: +91 376-237-0012, fax: +91 376-237-0011; Joshy Joseph, tel: +91 471 251-5476, fax: +91 471 249-1712

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Danaboyina Ramaiah

Photosciences and Photonics, Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram 695019, Kerala, India

Academy of Scientific and Innovative Research (AcSIR), CSIR-NIIST Campus, India

CSIR-North East Institute of Science and Technology, Jorhat 785 006, Assam, India

E-mail Address: joshyja@gmail.com

E-mail Address: joshy@niist.res.in

Correspondence to: Danaboyina Ramaiah, tel: +91 376-237-0012, fax: +91 376-237-0011; Joshy Joseph, tel: +91 471 251-5476, fax: +91 471 249-1712

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https://doi.org/10.1142/S1088424616501133Cited by:3 (Source: Crossref)

Abstract

Herein, we report the synthesis of two amphiphilic porphyrins having pyridinium moieties and their anion recognition properties in aqueous medium. The study of their interactions with various anions reveals that these porphyrins exhibit unique and selective interactions with CN^- ions when compared to the other anions. The addition of CN^- ions to an aqueous solution of the butyl porphyrin resulted in a hypochromicity of ca. 78% at 419 nm with a concomitant band formation at 449 nm in the absorption spectrum. Similarly, we observed ca. 82% quenching in the emission intensity by the addition of 12.5 M of CN^- ions in the fluorescence spectrum of the porphyrin mediated through aggregation. The limit of detection of CN^- ions was found to be ca. 49 ppb and the nature of interactions has been studied through various microscopic and spectroscopic techniques. These studies have confirmed 1,4-addition of CN^- ions to the pyridinium moiety of the porphyrin system, which led to the aggregation induced self-assembly resulting in the sensitive detection of CN^- ions through changes in absorbance and fluorescence intensity in aqueous medium.

Dedicated to Professor Tomás Torres on the occasion of his 65th birthday

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