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Synthesis, Solvatochromism and Fluorescence Quenching Studies of Naphthalene Diimide Dye by Nano graphene oxide

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Abstract

A naphthalene diimide dye with two side amine arm was prepared. Uv–Vis and fluorescence spectroscopic techniques are used for their photophysical and solvatochromic characteristics in different solvents. The Lippert-Mataga plot for naphthalene diimide demonstrated a negative linear dependence by increasing polarity. Results showed naphthalene diimide is more polar in the ground than in the excited state. A quenching study was conducted for interacting the naphthalene diimide as a fluorophore and graphene oxide as a quencher. Fluorescence quenching-based platforms in nanoscale have been used in sensing systems. Raman, FTIR, Uv–Vis and fluorescence spectroscopic techniques were used to study the quenching mechanism. The results indicated that graphene plays an effective quencher against the naphthalene diimide, with a quenching efficiency 91%. The Stern–Volmer analysis results show a mix of static and dynamic quenching mechanisms. The binding constant of the quencher-fluorophore and the number of binding sites have been reported. Thermodynamic parameters of their interaction were evaluated. The negative values of the Gibbs free energy confirm that the complexation process is spontaneous. Meanwhile, the positive entropy value confirms that the favorable pathway process.

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Acknowledgements

We want to thank Institute for Color Science and Technology, Tehran-Iran, for the facilities and materials to complete this project. Also, thank the Center of Excellence of "The Institute for Color Science and Technology" for their spiritual support.

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Authors and Affiliations

  1. Department of Polymer Engineering, Kish International Campus, University of Tehran, Kish Island, Iran

    Mojgan Mahdiani & Payam Zahedi

  2. Department of Organic Colorant, Institute for Color Science and Technology, Tehran, Iran

    Shohre Rouhani

  3. Center of Excellence for Color Science and Technology, Institute for Color Science and Technology, Tehran, Iran

    Shohre Rouhani

  4. Nano-Biopolymers Research Laboratory, School of Chemical Engineering, College of Engineering, University of Tehran, Tehran, Iran

    Payam Zahedi

Authors
  1. Mojgan Mahdiani
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  2. Shohre Rouhani
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Contributions

MM performed the experimental data acquisition and interpretation of the results. SR and PZ designed and wrote the entire manuscript. All authors participated in discussing the results and approved the final draft of the manuscript.

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Correspondence to Shohre Rouhani or Payam Zahedi.

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Mahdiani, M., Rouhani, S. & Zahedi, P. Synthesis, Solvatochromism and Fluorescence Quenching Studies of Naphthalene Diimide Dye by Nano graphene oxide. J Fluoresc 33, 2003–2014 (2023). https://doi.org/10.1007/s10895-023-03197-0

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