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Multicomponent Reaction Based Tolyl-substituted and Pyrene-Pyridine Conjugated Isomeric Ratiometric Fluorescent Probes: A Comparative Investigation of Photophysical and Hg(II)-Sensing Behaviors

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Abstract

Herein, the synthesis of pyrene conjugated 2,6-di-ortho-tolylpyridine and 2,6-di-para-tolylpyridine structural isomers were achieved efficiently through multicomponent Chichibabin pyridine synthesis reaction. The DFT, TD-DFT and experimental investigations were carried out to investigate the photophysical behaviors of the synthesized novel pyrene-pyridine based isomeric probes. Our studies revealed that, due to the continuous conjugation of the pyrene, pyridine and tolyl moieties, the dihedral angles of the trisubstituents on the central pyridine moiety significantly influences the photophysical properties of the synthesized novel pyrene based fluorescent probes. Further, we have comparatively investigated the sensing behaviors of the synthesized tolyl-substituted isomeric ratiometric fluorescent probes with metal ions, our studies reveals that both the ortho and para tolyl ratiometric fluorescent probes have distinct photoemissive properties in selectively sensing of Hg2+ ions. Our studies indicates that, the para-tolyl substituted isomer displays more red-shift in wavelength of emission band compared to its ortho isomer analogue during ratiometric fluorescent specific detection of Hg2+ ions.

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All the experimental and theoretical (DFT and TD-DFT) data generated or analyzed during this research work are included in this article and its supporting information file.

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Acknowledgements

The authors gratefully acknowledge the National Institute of Technology Andhra Pradesh for providing the departmental infrastructure. We also sincerely acknowledge Prof. K. V. Ramanujachary, Rowan University, USA, for providing LCMS data during initial stage synthesis of probes.

Funding

The financial support was received from National Institute of Technology Andhra Pradesh (SEED grant No. NITAP/SD-G/19/2020).

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Authors and Affiliations

  1. Department of Chemistry, School of Sciences, National Institute of Technology Andhra Pradesh, Tadepalligudem, 534101, Andhra Pradesh, India

    Raghvendra Niranjan, G. Durga Prasad & Surendra H. Mahadevegowda

  2. Organic Synthesis & Catalysis Lab, Department of Chemistry, National Institute of Technology Warangal, Hanumakonda, 506004, Telangana, India

    Mariyaraj Arockiaraj & Venkatachalam Rajeshkumar

  3. Department of Chemistry, National Institute of Technology, Tiruchirappalli, 620015, Tamil Nadu, India

    Kiruthika Nachimuthu & Jothi L. Nallasivam

  4. Chemical Sciences and Technology Division, CSIR-NIIST, Thiruvananthapuram, 695019, Kerala, India

    Simi Achankunju & Ishita Neogi

  5. Centre for Nano-Biosensors, Department of Prosthodontics, Saveetha Dental College and Hospitals, Saveetha Institute of Medical and Technical Sciences, Poonamallee High Road, Velappanchavadi, Chennai, 600077, Tamil Nadu, India

    Kotteswaran Velumani & Ashok K. Sundramoorthy

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Contributions

We confirm that the manuscript has been read and approved by all listed authors. The synthesis was performed by R. Niranjan. Absorption and emission studies were performed by R. Niranjan, G.D. Prasad, S. Achankunju, M. Arockiaraj, Ishita Neogi and V. Rajeshkumar. CV and IR characterizations were performed by K. Velumani and A.K. Sundramoorthy. Some partial experimental characterization done by K. Nachimuthu and J.L. Nallasivam. HRMS characterization and analysis done by V. Rajeshkumar. The DFT calculations, initial manuscript preparation and final manuscript corrections by S.H. Mahadevegowda.

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Correspondence to Surendra H. Mahadevegowda.

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Niranjan, R., Prasad, G.D., Achankunju, S. et al. Multicomponent Reaction Based Tolyl-substituted and Pyrene-Pyridine Conjugated Isomeric Ratiometric Fluorescent Probes: A Comparative Investigation of Photophysical and Hg(II)-Sensing Behaviors. J Fluoresc (2023). https://doi.org/10.1007/s10895-023-03467-x

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