Strong intramolecular charge-transfer effect strengthening naphthoquinone-based chemosensor: Experimental and theoretical evaluation

Dilmurod Sayfiddinov; Ramasamy Santhosh Kumar; Vignesh Krishnamoorthi Kaliannagounder; Palanisamy Ravichandiran; Kyung-Bin Cho; Cheol Sang Kim; Chan Hee Park; Kwan Seob Shim; Hyun Woo Choi; Byung-Hyun Park; Myung-Kwan Han; Dong Jin Yoo

doi:10.1016/j.saa.2024.123908

Strong intramolecular charge-transfer effect strengthening naphthoquinone-based chemosensor: Experimental and theoretical evaluation

Spectrochim Acta A Mol Biomol Spectrosc. 2024 Apr 15:311:123908. doi: 10.1016/j.saa.2024.123908. Epub 2024 Jan 24.

Affiliations

¹ Department of Life Science, Jeonbuk National University, Jeonju, Jeollabuk-do 54896, Republic of Korea; Department of Energy Storage/Conversion Engineering of Graduate School (BK21 FOUR), Hydrogen and Fuel Cell Research Center, Jeonbuk National University, Jeonju, Jeollabuk-do 54896, Republic of Korea.
² Department of Energy Storage/Conversion Engineering of Graduate School (BK21 FOUR), Hydrogen and Fuel Cell Research Center, Jeonbuk National University, Jeonju, Jeollabuk-do 54896, Republic of Korea.
³ Department of Bionanosystem Engineering, Jeonbuk National University, Jeonju, Jeollabuk-do 54896, Republic of Korea; Bionanotechnology and Bioconvergence Engineering, Graduate School, Jeonbuk National University, Jeonju, Jeollabuk-do 54896, Republic of Korea; Division of Mechanical Design Engineering, Jeonbuk National University, Jeonju, Jeollabuk-do 54896, Republic of Korea.
⁴ Department of Energy Storage/Conversion Engineering of Graduate School (BK21 FOUR), Hydrogen and Fuel Cell Research Center, Jeonbuk National University, Jeonju, Jeollabuk-do 54896, Republic of Korea; Analytical, HP Green R&D Centre, Hindustan Petroleum Corporation Limited, KIADB Industrial Area, Devangundi, Hoskote, Bengaluru, 562114 Karnataka, India.
⁵ Department of Chemistry and Research Institute of Physics and Chemistry, Jeonbuk National University, Jeonju 54896, Republic of Korea.
⁶ Department of Animal Biotechnology, College of Agriculture and Life Sciences, Jeonbuk National University, Jeollabuk-do 54896, Republic of Korea.
⁷ Department of Animal Science, College of Agriculture and Life Sciences, Jeonbuk National University, Jeollabuk-do 54896, Republic of Korea.
⁸ Department of Biochemistry, Jeonbuk National University Medical School, 567 Baekje-daero, Deokjin-gu, Jeonju-si, Jeollabuk-do 54896, Republic of Korea.
⁹ Department of Microbiology, Jeonbuk National University Medical School, 567 Baekje-daero, Deokjin-gu, Jeonju-si, Jeollabuk-do 54896, Republic of Korea.
¹⁰ Department of Life Science, Jeonbuk National University, Jeonju, Jeollabuk-do 54896, Republic of Korea; Department of Energy Storage/Conversion Engineering of Graduate School (BK21 FOUR), Hydrogen and Fuel Cell Research Center, Jeonbuk National University, Jeonju, Jeollabuk-do 54896, Republic of Korea. Electronic address: djyoo@jbnu.ac.kr.

PMID: 38330753
DOI: 10.1016/j.saa.2024.123908

Abstract

An aminophenol-linked naphthoquinone-based fluorometric and colorimetric chemosensor 2-chloro-3-((3-hydroxyphenyl) amino) naphthalene-1,4-dione (2CAN-Dione) was synthesized for selective detection of Sn²⁺ ion in aqueous solution. The amine and conversion of carbonyl into carboxyl groups play a vital role in the sensing mechanism when Sn²⁺ is added to 2CAN-Dione. Comprehensive characterization of the sensor was carried out using standard spectral and analytical approaches. Because of the intramolecular charge transfer (ICT) effect and the turn-on sensing mode, the strong fluorometric emission towards Sn²⁺ was observed at about 435 nm. The chemosensor exhibited good selectivity for Sn²⁺ in the presence of coexisting metal ions. An improved linear connection was established with a low limit of detection (0.167 μM). FT-IR, ¹H NMR, ¹³C NMR, and quantum chemistry methods were performed to verify the binding coordination mechanism. The chemosensing probe 2CAN-Dione was successfully employed in bioimaging investigations, demonstrating that it is a reliable fluorescent marker for Sn²⁺ in human cancer cells.

Keywords: Bioimaging of cancer cells; Metal ion sensing; Naphthoquinone-based chemosensor; Turn-on sensing.