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Red-emitting heteroleptic iridium(III) complexes: photophysical and cell labeling study

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Abstract

Two red-emitting heteroleptic iridium(III) complexes (Ir-p and Ir-q) were synthesized and their photophysical and biological properties were analyzed. After their structures have been confirmed by several techniques, such as 1H NMR, 13C NMR, FT–IR, UV–Vis, and MALDI TOF analyses, their luminescence behavior was investigated in ethanol and PBS (physiological medium, pH ~ 7.4) solutions. Emission spectra of both complexes are dominated by 3MLCT states at room temperature in ethanolic solution, but at 77 K the Ir-q exhibits the 3LC as the dominant emission state. The Ir-q complex shows one of the highest emission quantum yields, 11.5%, for a red emitter based on iridium(III) complexes in aerated PBS solution, with color coordinates (x;y) of (0.712;0.286). Moreover, both complexes display high potential to be used as a biological marker with excitation wavelengths above 400 nm, high water solubility (Ir-p 1838 μmol L−1, Ir-q 7601 μmol L−1), and distinct emission wavelengths from the biological autofluorescence. Their cytotoxicity was analyzed in CHO-k1 cells by MTT assays, and the IC50 was estimated as being higher than 131 μmol L−1 for Ir-p, and higher than 116 μmol L−1 for Ir-q. Concentrations above 70% of viability were used to perform cell imaging by confocal and fluorescence microscopies and the results suggest that the complexes were internalized by the cell membrane and they are staining the cytoplasm region.

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Acknowledgements

The authors are thankful to the Brazilian agencies FAPESP (Grant No.2019/26103-7), CNPq (Grant No.304003/2018-1) and CAPES for the financial research support. Felipe S. M. Canisares is particularly grateful to the São Paulo research Foundation (FAPESP Grant No.2015/03400-5) and Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES Grant No.88887.341772/2019-00) for the awarded scholarships. Laboratório de Difração de Raios X (FCT/UNESP), Núcleo de Inovação Tecnológica em Borracha Natural (FCT/UNESP), and Laboratório de Catálise Organometálica e Materiais (FCT/UNESP) for the cyclic voltammetry and FTIR measurements.

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Authors and Affiliations

  1. School of Technology and Sciences, São Paulo State University (Unesp), R. Roberto Simonsen, 305, Presidente Prudente, SP, 19060-900, Brazil

    Felipe S. M. Canisares, Alessandra M. G. Mutti, Edy F. Santana, Vytor C. Oliveira, Dalita G. S. M. Cavalcante, Aldo E. Job, Ana M. Pires & Sergio A. M. Lima

  2. Institute of Chemistry, São Paulo State University (Unesp), Araraquara, Brazil

    Felipe S. M. Canisares & Ana M. Pires

  3. Institute of Biosciences, Humanities and Exact Sciences, São Paulo State University (Unesp), São José Do Rio Preto, SP, Brazil

    Felipe S. M. Canisares & Ana M. Pires

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Canisares, F.S.M., Mutti, A.M.G., Santana, E.F. et al. Red-emitting heteroleptic iridium(III) complexes: photophysical and cell labeling study. Photochem Photobiol Sci 21, 1077–1090 (2022). https://doi.org/10.1007/s43630-022-00200-8

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