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Free base porphyrin–cyanine dye conjugate: synthesis and optical properties

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Abstract

The covalent combination of a cyanine dye (IR-783) with a tetraphenyl porphyrin unit through an ether linkage results in a photoactive system capable of producing singlet oxygen. The synthesis, characterization and photophysical properties of the resulting novel free base porphyrin–cyanine conjugate named TPPO-IR-783 (TOI) is reported. Excited state properties were studied in various solvents with differing polarity. The fluorescence is strongly solvent dependent, however this is not the case for singlet oxygen phosphorescence, which is only observed in tetrahydrofuran (THF), when comparing 8 different polar, non-polar and medium-polarity solvents. This novel type of porphyrin–cyanine photosensitizer has the ability to produce singlet oxygen and absorbs light at NIR wavelengths.

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Data availability

All available data belonging to this research can be found in this RDM repository: https://doi.org/10.21942/uva.22219864.v1

Abbreviations

A3B porphyrin:

Denotation of the substitution pattern of the meso-substituents on the porphyrin: 3 “A” substituents and 1 “B” substituent. In TPPOH (Fig. 3), A = phenyl group and B = 4-hydroxyphenyl group

A.U.:

Arbitrary units

DMF:

N, N-dimethylformamide

DMSO:

Dimethyl sulfoxide

ET:

Electron transfer

EtOH:

Ethanol

fs-TA:

Femtosecond transient absorption

IR:

Infrared

MeOH:

Methanol

ns-TA:

Nanosecond transient absorption

NIR:

Near-infrared

PBS:

Phosphate buffered saline

PS:

Photosensitizer

SOCT-ISC:

Spin–orbit charge transfer intersystem crossing

THF:

Tetrahydrofuran

TPP:

5,10,15,20-Tetraphenylporphyrin

TPPOH:

5-(4-Hydroxyphenyl)-10,15,20-triphenylporphyrin

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Acknowledgements

This project has received funding from the European Union’s Horizon 2020 research and innovation program under the Marie Sklodowska-Curie grant agreement no. 764837. We thank the Erasmus+ exchange program for supporting JPM. We thank Prof. Patrick Trouillas (Limoges) for the design of the Table of Contents picture. We thank Sarah Egan-Fraser for her contribution to this research, as summarized in the note above.

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Authors and Affiliations

  1. LABCiS - UR 22722, Faculty of Sciences and Technology, University of Limoges, 123 Avenue Albert Thomas, 87060, Limoges, France

    Dáire J. Gibbons, Yann Berbiguier, Nicolas Villandier & Stéphanie Leroy-Lhez

  2. Molecular Photonics Group, Van’t Hoff Institute for Molecular Sciences (HIMS), Universiteit van Amsterdam, Science Park 904, 1098 XH, Amsterdam, Netherlands

    Dáire J. Gibbons, Jordan P. Mulvaney & René M. Williams

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  1. Dáire J. Gibbons
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Correspondence to Stéphanie Leroy-Lhez or René M. Williams.

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Topical Collection in honor of Prof. Dr. A. M. (Fred) Brouwer and his contributions to science.

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Gibbons, D.J., Berbiguier, Y., Mulvaney, J.P. et al. Free base porphyrin–cyanine dye conjugate: synthesis and optical properties. Photochem Photobiol Sci 23, 163–176 (2024). https://doi.org/10.1007/s43630-023-00510-5

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