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Fluorescence Sensing of pH and p-Nitrophenol Using an AIEE Active Pyridoxal Derived Schiff Base

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Abstract

An easy-to-prepare aggregation-induced emission enhancement (AIEE) active Schiff base NPY was synthesized by condensing vitamin B6 cofactor pyridoxal with 3-hydroxy-2-naphthoic hydrazide, and employed for the fluorescent sensing of pH and p-nitrophenol (p-NP). The AIEE phenomenon of NPY was investigated in mixed DMSO/H2O medium. The weakly yellow-fluorescent NPY (λem = 535 nm) in pure DMSO turned to a bright cyan-fluorescent NPY (λem = 490 nm) upon addition of poor solvent water. The DLS and SEM analyses supported the self-aggregation of NPY that restricted the intramolecular rotation and activated the excited state intramolecular proton transfer (ESIPT) process. The AIEE luminogen (AIEEgen) NPY containing 90% of water fraction (fwater) was employed for the fluorescent sensing of pH. AIEEgen NPY displays three distinct fluorescent pH windows: non-fluorescent below pH 3.0 and above pH 10.0, cyan fluorescent between pH 3.0 to 8.0, and yellow fluorescent between pH 8.0 to 10.0. AIEEgen NPY was also applied for the detection of nitroaromatics in HEPES buffer (10% DMSO, 10 mM, pH 7.0). The addition of p-NP selectively quenched the fluorescent intensity of AIEEgen NPY with an estimated detection limit of 1.73 µM. The analytical utility of AIEEgen NPY was examined by quantifying p-NP in different real water samples.

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Authors and Affiliations

  1. Department of Chemistry, Sardar Vallabhbhai National Institute Technology, 395007, Surat, Gujarat, India

    Dhvani A. Patel & Suban K. Sahoo

  2. Department of Chemistry, Sathyabama Institute of Science and Technology, 600119, Chennai, India

    Thangaraj Anand

  3. Department of Chemistry, School of Advance Sciences, Vellore Institute of Technology, 632014, Vellore, Tamil Nadu, India

    Ashok Kumar SK

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Contributions

All authors contributed to the study. The Investigation, Validation, Formal analysis, Data curation, Writing-original draft were performed by Dhvani A. Patel. Thangaraj Anand helps in Writing-original draft. Ashok Kumar SK helps in Formal analysis. The Conceptualization, Resources, Supervision, and Writing-review & editing were performed by Suban K Sahoo.

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Correspondence to Suban K. Sahoo.

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Patel, D.A., Anand, T., SK, A.K. et al. Fluorescence Sensing of pH and p-Nitrophenol Using an AIEE Active Pyridoxal Derived Schiff Base. J Fluoresc 33, 1431–1441 (2023). https://doi.org/10.1007/s10895-023-03167-6

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