Lorena Vogt

Supramolecular ¹O₂ Storage Systems based on Pyridone-Subphthalocyanine-Dyads

Singlet Oxygen (¹O₂ ), a reactive oxygen species, has a cytotoxic effect on living cells and can be used against bacteria, viruses and in photodynamic therapy. Instead of generating ¹O₂ in situ at the intended site of action by the interaction of light, oxygen and an appropriate photosensitizer, the delayed provision of reactive oxygen through the thermal decomposition of an endoperoxide (EPO) has recently received broad attention.¹ In that context, self-sensitized EPO-forming dyads, in which EPO-forming units are covalently attached to photosensitizers, have become increasingly important.^1-4 I am currently investigating the combination of pyridones as EPO-forming units and subphthalocyanines (SubPc) as photosensitizers.

MATSUMOTO et al. recognized in 2005 the reversible binding of ¹O₂ by pyridones, which are particularly suitable for biological applications due to their solubility parameters in aqueous media.⁵The high ¹O₂-quantum yield of subphthalocyanines and their cone-shaped topology, which minimizes aggregation, make them particularly interesting for these dyads.⁶

The focus of my work is the synthesis of covalently and supramolecularly attached pyridone-SubPc-dyads, the generation of ¹O₂ by the irradiation of the photosensitizer (SubPc), the self-sensitized EPO formation by cycloaddition of ¹O₂ to pyridones and the delayed and controlled release of reactive oxygen via a thermal cycloreversion process.

[1] M.A. Filatov, M.O. Senge, Mol. Syst. Des. Eng., 2016, 1, 258-272.
[2] D. Rihter, M.E. Kenney, W.E. Ford, M.A. J. Rodgers, J. Am. Chem. Soc., 1993, 115, 8146-8152.
[3] W. Freyer, H. Stiel, M. Hild, K. Teuchner, D. Leupold, Photochem. Photobiol., 1997, 66, 696-604.
[4] S. Callaghan, M. A. Filatov, E. Sitte, H. Savoie, R. W. Boyle, K. J. Flanagan, M. O. Senge, 
     Photochem, Photobiol. Sci., 2017, 16, 1371-1374.
[5] M. Matsumoto, M. Yamada, N. Watanabe, Chem. Commun., 2005, 4, 483-485.
[6] C. Claessens, D. González-Rodriguez, T. Torres, Chem. Rev., 2002, 102, 835-853.

Intramolecular photosensitization for singlet oxygen trapping: Assembly of a subphthalocyanine-anthracene dyad, L. Vogt, R. Münnich, R. Faust, J. Porphyrins Phthalocyanines, 2025, 29, 367-372.
DOI: 10.1142/S1088424625500282

L. Vogt, R. Faust
"Subphthalocyanine-Anthracene-Dyad as a Singlet Oxygen Storage System”, Flashtalk, GDCh Wissenschaftsforum (WiFo-2019), Aachen, September 16-18, 2019.

L. Vogt, A. Petersen, V. Viereckt, F. Abendroth, O. Vázquez, R. Faust
“Thermally controlled Singlet Oxygen Storage and Release from a SubPc-Pyr-Dyad in HeLa Cells”, 14^th International Conference on Porphyrins and Phthalocyanines (ICPP-14), Kyoto, Japan, Juni 28 - Juli 03, 2026, Abstract S02-07.

L. Vogt, R. Faust
“SubPc-Pyridone-Dyads for Storage and delayed Release of Singlet Oxygen”, 13^th International Conference on Porphyrins and Phthalocyanines (ICPP-13), Niagra Falls NY, USA, Juni 23 - 28, 2024, Abstract S01-P-005.

L. Vogt, R. Faust
“Controlled Storage and Release of Singlet Oxygen via Pyridone-Subphthalocyanine-Dyads”, GDCh-Wissenschaftsforum (WiFo) Chemie 2023, Leipzig, September 04 - 06, 2023.

L. Vogt, R. Faust
“Controlled Storage and Release of Singlet Oxygen via Pyridone-Subphthalocyanine-Dyads”, 12^th International Conference on Porphyrins and Phthalocyanines (ICPP-12), Madrid, Spanien, Juni 10 - 15, 2022, Abstract S01-P-011.

L. Vogt, A. Petersen, R. Faust
„A Pyridone-SubPc-Dyad as a ¹O₂ Storage System: Self-sensitized EPO formation and thermal release of ¹O₂“, GDCh-Wissenschaftsforum (WiFo) Chemie 2021, online, August 29 - September 01, 2021.

L. Vogt, R. Faust
“A Pyridone-SubPc-Dyad as a ¹O₂ Storage System: Self-sensitized EPO formation and thermal release of ¹O₂", 11^thInternational Conference on Porphyrins and Phthalocyanines (ICPP-11), online, Juni 28 - Juli 03, 2021.

L. Vogt, R. Faust
“Subphthalocyanine-Anthracene-Dyad as a Singlet Oxygen Storage System”, CINSaT autumn colloquium, Kassel, October 16, 2019.

L. Vogt, R. Faust
“Subphthalocyanine-Anthracene-Dyad as a Singlet Oxygen Storage System”, GDCh Wissenschaftsforum (WiFo-2019), Aachen, September 16-18, 2019.

L. Höfer, R. Münnich, R. Faust
“Axially modified Subporphyrazines as Singlet Oxygen Storage Systems”, 10^th International Conference on Porphyrins and Phthalocyanines (ICPP-10), München, July 1-6, 2018.

L. Höfer
“Axial funktionalisierte Subporphyrazine als Singulett-Sauerstoff-Transporter”, Wissenschaftliche Hausarbeit zum 1. Staatsexamen, Universität Kassel, 2018.