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Synthesis of highly water soluble tetrabenzoporphyrins and their application toward photodynamic therapy

https://doi.org/10.1142/S1088424619501785

Moss, Austen; Zhou, Zehua; Jiang, Lin; Vicente, M. Graça; Wang, Hong (January 2020, Journal of Porphyrins and Phthalocyanines)

Novel tetraaryl-(pyridinium-4-yl)-tetrabenzoporphyrins have been successfully synthesized via a Heck-based sequence reaction. These tetrabenzoporphyrins were substituted with eight pyridyl groups at the fused benzene rings. Methylation of the pyridyl groups with methyl iodide afforded highly water soluble tetrabenzoporphyrins carrying eight ionic groups. The extended [Formula: see text]-conjugation broadened and red-shifted the absorption band of these porphyrins to 650–750 nm. These cationic tetrabenzoporphyrins showed non-toxicity in the dark up to 100 uM. High phototoxicity with IC[Formula: see text] values lower than 18 [Formula: see text]M were obtained for these tetrabenzoporphyrins.
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Nickel(II) Bisporphyrin‐Fused Pentacenes Exhibiting Abnormal High Stability

https://doi.org/10.1002/ange.202008076

Hu, Yi; Thomas, Michael B.; Webre, Whitney A.; Moss, Austen; Jinadasa, R. G. Waruna; Nesterov, Vladimir N.; D'Souza, Francis; Wang, Hong (November 2020, Angewandte Chemie)

Abstract A series of largely π‐extended multichromophoric molecules including cross‐conjugated, half cross‐conjugated, conjugation‐interrupted and linearly conjugated systems were synthesized and characterized. These multichromophoric molecular systems revealed interesting structural‐property relationships. Bisporphyrin‐fused pentacenesPen‐1 bandPen‐2 ashowed rich redox chemistry with 7 and 8 observable redox states, respectively. The linearly‐conjugated bisporphyrin‐fused pentacenes (Pen‐1 bandPen‐2 a) possess much narrower HOMO–LUMO gaps (1.65 and 1.42 eV redox, respectively) and higher HOMO energy levels than those of their pentacene analogues (2.23 and 2.01 eV redox, respectively), similar to those of much less stable hexacenes and heptacenes. An estimated half‐life of >945 h was obtained for bisporphyrin‐fused pentacenePen‐2 a, which is much longer than that of its pentacene analogue (BPE‐P, half‐life, 33 h).
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Nickel(II) Bisporphyrin‐Fused Pentacenes Exhibiting Abnormal High Stability

https://doi.org/10.1002/anie.202008076

Hu, Yi; Thomas, Michael B.; Webre, Whitney A.; Moss, Austen; Jinadasa, R. G. Waruna; Nesterov, Vladimir N.; D'Souza, Francis; Wang, Hong (November 2020, Angewandte Chemie International Edition)

Abstract A series of largely π‐extended multichromophoric molecules including cross‐conjugated, half cross‐conjugated, conjugation‐interrupted and linearly conjugated systems were synthesized and characterized. These multichromophoric molecular systems revealed interesting structural‐property relationships. Bisporphyrin‐fused pentacenesPen‐1 bandPen‐2 ashowed rich redox chemistry with 7 and 8 observable redox states, respectively. The linearly‐conjugated bisporphyrin‐fused pentacenes (Pen‐1 bandPen‐2 a) possess much narrower HOMO–LUMO gaps (1.65 and 1.42 eV redox, respectively) and higher HOMO energy levels than those of their pentacene analogues (2.23 and 2.01 eV redox, respectively), similar to those of much less stable hexacenes and heptacenes. An estimated half‐life of >945 h was obtained for bisporphyrin‐fused pentacenePen‐2 a, which is much longer than that of its pentacene analogue (BPE‐P, half‐life, 33 h).
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