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Probing the ESIPT process in 2-amino-1,4-naphthoquinone: thermodynamics properties, solvent effect and chemometric analysis

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Abstract

The developing of fluorescent probes for disease diagnosis is a very important task, which favors precision in the diagnosis and success in the treatment. Recently, amino-naphthoquinone derivatives showed to be efficient fluorescent probes for disease diagnosis. Those compounds exhibit excited-state intramolecular proton transfer (ESIPT), which is the main mechanism responsible for their use as fluorescent probes. The understanding of the ESIPT mechanism for naphthoquinones is an important way of developing more efficient and selective fluorescent probes. In this work, the ESIPT process for ANQ was performed at the TD-DFT/CAM-B3LYP/DGTZVP and DFT/B3LYP/DGTZVP level for the electronic and geometric studies. These parameters were selected for the PCA analysis. The solvent effect was investigated by using PCM and IEF-PCM in chloroform, water and methanol. 2-Amino-1,4-naphthoquinone (ANQ) showed blue emission for fluorescence, having keto–keto* absorption at 4.50 eV and the enol–enol* decay at 2.75 eV. The solvent effect was evaluated, and the ESIPT process of ANQ was favorable in nonpolar and polar solvents. Furthermore, the thermodynamics properties showed that the ESIPT is favorable with a proton transfer equilibrium constant of ~105.

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Acknowledgments

The authors thank the Brazilian agencies FAPEMIG, CAPES and CNPq for the financial support of this research and UFLA for infrastructure and encouragement in this work. T.C.R. thanks also for the invited professor position at the Czech Republic Center for Basic and Applied Research.

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Authors and Affiliations

  1. Chemistry Department, Federal University of Lavras, Lavras, Minas Gerais, Brazil

    Eduardo Pereira Rocha & Teodorico Castro Ramalho

  2. Center for Basic and Applied Research, Faculty of Informatics and Management, University of Hradec Kralove, Hradec Kralove, Czech Republic

    Teodorico Castro Ramalho

  3. Federal Institute of Education, Science and Technology Southeast of Minas Gerais, Rio Pomba, Minas Gerais, Brazil

    Eduardo Pereira Rocha

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  1. Eduardo Pereira Rocha
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Correspondence to Teodorico Castro Ramalho.

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Published as part of the special collection of articles “CHITEL 2015 - Torino - Italy”.

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Rocha, E.P., Ramalho, T.C. Probing the ESIPT process in 2-amino-1,4-naphthoquinone: thermodynamics properties, solvent effect and chemometric analysis. Theor Chem Acc 135, 39 (2016). https://doi.org/10.1007/s00214-015-1786-4

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