A Study of Small Molecule-Based Rhodamine-Derived Chemosensors and Their Implications in Environmental and Biological Systems from 2012 to 2021: Latest Advancement and Future Prospects

Overview

Journal J Fluoresc

Specialties Biophysics
Chemistry

Date 2023 May 22

PMID 37212978

Authors

Raguraman Lalitha

Sivan Velmathi

Affiliations

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Abstract

Rhodamine-based chemosensors have sparked considerable interest in recent years due to their remarkable photophysical properties, which include high absorption coefficients, exceptional quantum yields, improved photostability, and significant red shifts. This article presents an overview of the diverse fluorometric, and colorimetric sensors produced from rhodamine, as well as their applications in a wide range of fields. The ability of rhodamine-based chemosensors to detect a wide range of metal ions, including Hg, Al, Cr, Cu, Fe, Fe, Cd, Sn, Zn, and Pb, is one of their major advantages. Other applications of these sensors include dual analytes, multianalytes, and relay recognition of dual analytes. Rhodamine-based probes can also detect noble metal ions such as Au, Ag, and Pt. They have been used to detect pH, biological species, reactive oxygen and nitrogen species, anions, and nerve agents in addition to metal ions. The probes have been engineered to undergo colorimetric or fluorometric changes upon binding to specific analytes, rendering them highly selective and sensitive by ring-opening via different mechanisms such as Photoinduced Electron Transfer (PET), Chelation Enhanced Fluorescence (CHEF), Intramolecular Charge Transfer (ICT), and Fluorescence Resonance Energy Transfer (FRET). For improved sensing performance, light-harvesting dendritic systems based on rhodamine conjugates has also been explored for enhanced sensing performance. These dendritic arrangements permit the incorporation of numerous rhodamine units, resulting in an improvement in signal amplification and sensitivity. The probes have been utilised extensively for imaging biological samples, including imaging of living cells, and for environmental research. Moreover, they have been combined into logic gates for the construction of molecular computing systems. The usage of rhodamine-based chemosensors has created significant potential in a range of disciplines, including biological and environmental sensing as well as logic gate applications. This study focuses on the work published between 2012 and 2021 and emphasises the enormous research and development potential of these probes.

References

Chen X, Pradhan T, Wang F, Kim J, Yoon J . Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives. Chem Rev. 2011; 112(3):1910-56. DOI: 10.1021/cr200201z. View

Kim H, Lee M, Kim H, Kim J, Yoon J . A new trend in rhodamine-based chemosensors: application of spirolactam ring-opening to sensing ions. Chem Soc Rev. 2008; 37(8):1465-72. DOI: 10.1039/b802497a. View

Moon H, Park J, Tae J . Fluorescent Probes Based on Rhodamine Hydrazides and Hydroxamates. Chem Rec. 2015; 16(1):124-40. DOI: 10.1002/tcr.201500226. View

Beija M, Afonso C, Martinho J . Synthesis and applications of Rhodamine derivatives as fluorescent probes. Chem Soc Rev. 2009; 38(8):2410-33. DOI: 10.1039/b901612k. View

Bera K, Das A, Nag M, Basak S . Development of a rhodamine-rhodanine-based fluorescent mercury sensor and its use to monitor real-time uptake and distribution of inorganic mercury in live zebrafish larvae. Anal Chem. 2014; 86(5):2740-6. DOI: 10.1021/ac404160v. View

Mao Y, Hong M, Liu A, Xu D . Highly Selective and Sensitive Detection of Hg(II) from HgCl2 by a Simple Rhodamine-Based Fluorescent Sensor. J Fluoresc. 2015; 25(3):755-61. DOI: 10.1007/s10895-015-1564-7. View

Li D, Li C, Li Y, Li Z, Xu F . Rhodamine-based chemodosimeter for fluorescent determination of Hg(2+) in 100% aqueous solution and in living cells. Anal Chim Acta. 2016; 934:218-25. DOI: 10.1016/j.aca.2016.05.050. View

Jiao Y, Zhang L, Zhou P . A rhodamine B-based fluorescent sensor toward highly selective mercury (II) ions detection. Talanta. 2016; 150:14-9. DOI: 10.1016/j.talanta.2015.11.065. View

Rasheed T, Nabeel F, Bilal M, Zhao Y, Adeel M, Iqbal H . Aqueous monitoring of toxic mercury through a rhodamine-based fluorescent sensor. Math Biosci Eng. 2019; 16(4):1861-1873. DOI: 10.3934/mbe.2019090. View

10.

Cicekbilek F, Yilmaz B, Bayrakci M, Gezici O . An Application of a Schiff-Base Type Reaction in the Synthesis of a New Rhodamine-Based Hg(II)-Sensing Agent. J Fluoresc. 2019; 29(6):1349-1358. DOI: 10.1007/s10895-019-02462-5. View

11.

Hazra S, Bodhak C, Chowdhury S, Sanyal D, Mandal S, Chattopadhyay K . A novel tryptamine-appended rhodamine-based chemosensor for selective detection of Hg present in aqueous medium and its biological applications. Anal Bioanal Chem. 2019; 411(6):1143-1157. DOI: 10.1007/s00216-018-1546-0. View

12.

Li X, Li X, Zhao H, Kang H, Fan C, Liu G . A Novel Diarylethene-rhodamine Unit Based Chemosensor for Fluorimetric and Colorimetric Detection of Hg. J Fluoresc. 2021; 31(5):1513-1523. DOI: 10.1007/s10895-021-02775-4. View

13.

Gupta V, Mergu N, Kumawat L, Singh A . A reversible fluorescence "off-on-off" sensor for sequential detection of aluminum and acetate/fluoride ions. Talanta. 2015; 144:80-9. DOI: 10.1016/j.talanta.2015.05.053. View

14.

Yang L, Tang A, Wang P, Yang S . Switching of C-C and C-N Coupling/Cleavage for Hypersensitive Detection of Cu by a Catalytically Mediated 2-Aminoimidazolyl-Tailored Six-Membered Rhodamine Probe. Org Lett. 2020; 22(21):8234-8239. DOI: 10.1021/acs.orglett.0c02814. View

15.

Liu Y, Zhao C, Zhao X, Liu H, Wang Y, Du Y . A selective N,N-dithenoyl-rhodamine based fluorescent probe for Fe detection in aqueous and living cells. J Environ Sci (China). 2020; 90:180-188. DOI: 10.1016/j.jes.2019.12.005. View

16.

Wang Q, Li C, Zou Y, Wang H, Yi T, Huang C . A highly selective fluorescence sensor for Tin (Sn4+) and its application in imaging live cells. Org Biomol Chem. 2012; 10(33):6740-6. DOI: 10.1039/c2ob25895a. View

17.

Mahapatra A, Manna S, Mandal D, Mukhopadhyay C . Highly sensitive and selective rhodamine-based "off-on" reversible chemosensor for tin (Sn4+) and imaging in living cells. Inorg Chem. 2013; 52(19):10825-34. DOI: 10.1021/ic4007026. View

18.

Karmegam M, Karuppannan S, Leslee D, Subramanian S, Gandhi S . Phenothiazine-rhodamine-based colorimetric and fluorogenic 'turn-on' sensor for Zn and bioimaging studies in live cells. Luminescence. 2019; 35(1):90-97. DOI: 10.1002/bio.3701. View

19.

Aich K, Goswami S, Das S, Mukhopadhyay C, Quah C, Fun H . Cd(2+) Triggered the FRET "ON": A New Molecular Switch for the Ratiometric Detection of Cd(2+) with Live-Cell Imaging and Bound X-ray Structure. Inorg Chem. 2015; 54(15):7309-15. DOI: 10.1021/acs.inorgchem.5b00784. View

20.

Sakthivel P, Sekar K, Sivaraman G, Singaravadivel S . Rhodamine Diaminomaleonitrile Conjugate as a Novel Colorimetric Fluorescent Sensor for Recognition of Cd Ion. J Fluoresc. 2017; 27(3):1109-1115. DOI: 10.1007/s10895-017-2046-x. View