A novel terephthalaldehyde based turn-on fluorescent chemosensor for Cu2+ and its application in imaging of living cells

Pritam Torawane; Karunesh Keshav; Mukesh K. Kumawat; Rohit Srivastava; Thangaraj Anand; Suban Sahoo; Amulrao Borse; Anil Kuwar

doi:10.1039/C7PP00182G

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A novel terephthalaldehyde based turn-on fluorescent chemosensor for Cu²⁺ and its application in imaging of living cells†

Pritam Torawane,

^a Karunesh Keshav,^b Mukesh K. Kumawat,

^c Rohit Srivastava,

^c Thangaraj Anand,^d Suban Sahoo,

^d Amulrao Borse*^a and Anil Kuwar

*^a

Author affiliations

* Corresponding authors

^a School of Chemical Sciences, North Maharashtra University, Jalgaon-425001, Maharashtra, India
E-mail: kuwaras@gmail.com, amulborse@gmail.com
Fax: +91-257-2257403
Tel: +91-257-2257432

^b Department of Chemistry, Indian Institute of Technology, Powai, Mumbai, Maharashtra, India

^c Department of Biosciences and Bioengineering, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India

^d Department of Applied Chemistry, SV National Institute Technology, Surat, Gujrat, India

Abstract

A new terephthaldehyde-based chemosensor 1 bearing an aminophenol recognition unit has been synthesized and applied to the fluorescent sensing of metal ions. Molecular system 1 acts as a highly selective and sensitive fluorescence turn-on sensor for Cu²⁺. The sensing mechanism has been explored. It is proposed that Cu²⁺ binds with the imine and hydroxyl moiety of 1 in 1 : 2 binding stoichiometry, thereby enhancing the fluorescence at 386 nm. The detection limit and association constant (K_a) of 1 with Cu²⁺ were found to be 0.62 μM and 6.67 × 10⁴ M⁻¹, respectively. Chemosensor 1 has shown excellent specificity towards Cu²⁺ and has been successfully applied to the determination of Cu²⁺ in live L929 cells.

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Article information

DOI: https://doi.org/10.1039/C7PP00182G
Article type: Paper
Submitted: 19 May 2017
Accepted: 20 Jul 2017
First published: 21 Jul 2017

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Photochem. Photobiol. Sci., 2017,16, 1464-1470

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A novel terephthalaldehyde based turn-on fluorescent chemosensor for Cu²⁺ and its application in imaging of living cells

P. Torawane, K. Keshav, M. K. Kumawat, R. Srivastava, T. Anand, S. Sahoo, A. Borse and A. Kuwar, Photochem. Photobiol. Sci., 2017, 16, 1464 DOI: 10.1039/C7PP00182G

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Photochemical & Photobiological Sciences