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Photophysical Behaviour of Novel Quaternary Pyrenoyl Salts and Their Sensitivity Towards Bile Salt Micellization

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Abstract

The present work describes the synthesis and characterization of pyrene derivatives, N-(1-Pyrenoylmethyl) pyridinium bromide (PM-PB) and N-(1-Pyrenoylmethyl)-N,N,N-triethylammonium bromide (PM-TAB). The photophysical behavior of these molecules has been studied in various protic and aprotic solvents. Using steady state fluorescence intensity, fluorescence anisotropy and dynamic fluorescence lifetime studies, the sensitivity of these molecules towards the micellization process of bile salts has been monitored. These derivatives have been effectively used in estimating critical micellar concentration (CMC) of bile salt, sodium deoxycholate (NaDC).

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Data Availability

All the data that have been referred to in the manuscript without being included have been given in the Supporting Information. Figures showing 1H-NMR spectrum (DMSO-d6) of N-1-(Pyrenoylmethyl) pyridinium bromide (Fig. S1), 13C-NMR spectrum (DMSO-d6) of N-1-(Pyrenoylmethyl) pyridinium bromide (Fig. S2), 1H-NMR spectrum (DMSO-d6) of N-(1-Pyrenoylmethyl)-N,N,N-triethylammonium bromide (Fig. S3), 13C-NMR spectrum (DMSO-d6) of N-(1-Pyrenoylmethyl)-N,N,N-triethylammonium bromide (Fig. S4), emission spectra of PM-PB and PM-TAB in solvents of different polarity (Fig. S5), emission spectra of PM-PB and PM-TAB with increasing NaDC concentration from 0 to 18 mM (Fig. S6) are available in the Supporting Information.

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Acknowledgements

The authors thank Prof. K. K. Balasubramanian and Prof A. K. Mishra of IIT Madras, India, for their valuable discussion and help in collecting fluorescence lifetime data.

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Authors and Affiliations

  1. B.S. Abdur Rahman Crescent Institute of Science and Technology, Chennai, 600048, India

    M. Saravanan, S. Dhivakar & S. Kutti Rani

  2. School of Chemistry, Gangadhar Meher University, Sambalpur, Odisha, 768004, India

    M. Mohapatra

  3. Polyvalent Organics, Chennai, 600032, India

    K. Vijayakumaran

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  1. M. Saravanan
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  2. S. Dhivakar
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  3. M. Mohapatra
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  4. S. Kutti Rani
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  5. K. Vijayakumaran
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Contributions

Synthesis, chemical characterization has been done by MS, SD, and supervised by SKR, and KV. Photophysical studies have been done by MS, MM, and supervised by MM. All authors read and approved the final manuscript.

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Correspondence to M. Mohapatra or K. Vijayakumaran.

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Saravanan, M., Dhivakar, S., Mohapatra, M. et al. Photophysical Behaviour of Novel Quaternary Pyrenoyl Salts and Their Sensitivity Towards Bile Salt Micellization. J Fluoresc 32, 1557–1563 (2022). https://doi.org/10.1007/s10895-022-02955-w

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  • DOI: https://doi.org/10.1007/s10895-022-02955-w

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