Abstract
Carbazole is a unique template associated with several biological activities. It is due to the diverse and versatile biological properties of carbazole derivatives that they are of immense interest to the research community. 1-keto-1,2,3,4-tetrahydrocarbazoles are important synthetic intermediates to obtain carbazole derivatives. Several members of this family emit fluorescence on photoexcitation. In the context of biochemical and biophysical research, designing and characterising small molecule environment sensitive fluorophores is extremely significant. This article aims to be a state of the art review with synthetic and photophysical details of a variety of fluorophores based on 1-keto-1,2,3,4-tetrahydrocarbazole skeleton.
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References
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Acknowledgements
The author would like to acknowledge the financial assistance provided by the Department of Science & Technology and Biotechnology, Government of West Bengal, India (Memo No. 100(Sanc.)/STBT-11012(25)/5/2019-ST SEC dated 28/04/2022). The author would like to acknowledge the guidance of Prof. Samita Basu and Prof. Chandan Saha for introducing him to the field of 'Organic Photochemistry'.
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Department of Science & Technology and Biotechnology, Government of West Bengal, India (Memo No. 100(Sanc.)/STBT-11012(25)/5/2019-ST SEC dated 28/04/2022).
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Highlights
• The excited state properties of MDKTHC vary dramatically depending on the immediate H-bonding environment.
• MDKTHC emission maxima shift towards red as the solvents' ET(30) value increases.
• When the solvent is changed from polar aprotic to aqueous, a significant Stokes’s shift (often greater than 100 nm) is observed in the case of MDKTHC.
• MDKTHC behaves differently in different microheterogeneous environments.
• Each micellar environment exhibits abrupt changes in the emission profile of MDKTHC around the CMC.
• The emission spectrum of buffered solution of MDKTHC is found to be significantly perturbed upon binding with the proteins.
• A quantitative analysis of the emission intensity data on the Benesi–Hildebrand equation reveals that the MDKTHC:β-CD complex has a 1:1 stoichiometry.
• In polar aprotic solvents, organic bases TEA and DMA quench MDKTHC fluorescence.
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Mitra, A.K. The Journey of 1-Keto-1,2,3,4-Tetrahydrocarbazole Based Fluorophores: From Inception to Implementation. J Fluoresc 32, 2023–2052 (2022). https://doi.org/10.1007/s10895-022-03004-2
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DOI: https://doi.org/10.1007/s10895-022-03004-2