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Benzazole-Based ESIPT Fluorophores: Proton Transfer from the Chalcogen Perspective. A Combined Theoretical and Experimental Study

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Abstract

In this study, we present a comprehensive photophysical investigation of ESIPT-reactive benzazole derivatives in both solution and the solid state. These derivatives incorporate different chalcogen atoms (O, S, and Se) into their structures, and we explore how these variations impact their electronic properties in both ground and excited states. Changes in the UV-Vis absorption and fluorescence emission spectra were analyzed and correlated with the chalcogen atom and solvent polarity. In general, the spectral band of the benzazole derivative containing selenium was redshifted in both the ground and excited states compared to that of its oxygen and sulfur counterparts. Furthermore, we observed that the solvent played a distinctive role in influencing the ESIPT process within these compounds, underscoring once again the significant influence of the chalcogen atom on their photophysical behavior. Theoretical calculations provided a deeper understanding of the molecular dynamics, electronic structures, and photophysical properties of these compounds. These calculations highlighted the effect of chalcogen atoms on the molecular geometry, absorption and emission characteristics, and intramolecular hydrogen bonding, revealing intricate details of the ESIPT mechanism. The integration of experimental and computational data offers a detailed view of the structural and electronic factors governing the photophysical behavior of benzazole derivatives.

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Acknowledgements

Theoretical calculations were performed using the Lobo Carneiro supercomputer from Núcleo Avançado de Computação de Alto Desemprenho (NACAD) under Project ID a20006 and the Sagarana Cluster from CEPAD—Centro de Processamento de Alto Desempenho ICB/UFMG. The authors would also like to thank the National Laboratory for Scientific Computing (LNCC/MCTI, Brazil) for providing the HPC resources of the SDumont supercomputer, which contributed to the research results reported in this paper. (URL:http://sdumont.lncc.br).

Funding

This research was funded by FAPERGS (17/2551-0000968-1 and PRONEX), CNPq (305954/2019-9) and Coordenação de Aperfeiçoamento de Pessoal de Nível Superior—Brasil (CAPES) – Finance Code 001 for the financial support.

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  1. Instituto de Química, Departamento de Química Orgânica, Universidade Federal Do Rio Grande Do Sul (UFRGS), PO Box 15003, Porto Alegre, Rio Grande Do Sul, ZIP Code91501-970, Brazil

    Louise Kommers Reimann, Bianca Thaís Dalberto, Paulo Henrique Schneider, Henrique de Castro Silva Junior & Fabiano Severo Rodembusch

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  1. Louise Kommers Reimann
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L.K.R.: Formal analysis, editing, and review of the manuscript. B.T.D.: Formal analysis. H.C.S.: Data Validation, formal analysis, editing, and review of the manuscript. P.H.S.: Resources, data validation, editing and review of the manuscript, funding acquisition. F.S.R.: Conceptualization, data validation, resources, editing and review of the manuscript, funding acquisition. project administration

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Correspondence to Henrique de Castro Silva Junior or Fabiano Severo Rodembusch.

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Reimann, L.K., Dalberto, B.T., Schneider, P.H. et al. Benzazole-Based ESIPT Fluorophores: Proton Transfer from the Chalcogen Perspective. A Combined Theoretical and Experimental Study. J Fluoresc (2024). https://doi.org/10.1007/s10895-024-03595-y

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