Improvement of the ON/OFF Switching Performance of a pH‐Activatable Porphyrin Derivative by the Introduction of Phosphorus(V) | Zendy

Horiuchi Hiroaki | Zendy; Isogai Masataka | Zendy; Hirakawa Kazutaka | Zendy; Okutsu Tetsuo | Zendy

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Improvement of the ON/OFF Switching Performance of a pH‐Activatable Porphyrin Derivative by the Introduction of Phosphorus(V)

Author(s) -

Horiuchi Hiroaki,

Isogai Masataka,

Hirakawa Kazutaka,

Okutsu Tetsuo

Publication year - 2019

Publication title -

chemphotochem

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.13

H-Index - 18

ISSN - 2367-0932

DOI - 10.1002/cptc.201800248

Subject(s) - singlet oxygen , porphyrin , photosensitizer , chemistry , photochemistry , photodynamic therapy , quantum yield , aniline , conjugate , tetraphenylporphyrin , oxygen , derivative (finance) , fluorescence , organic chemistry , mathematical analysis , physics , mathematics , quantum mechanics , financial economics , economics

An activatable photosensitizer for singlet oxygen is of significance due to its potential application in tumor‐specific photodynamic therapy and diagnosis. In this study, a pH‐activatable system that enables the specific photosensitization of singlet oxygen at a low pH value was developed based on the complexation of a porphyrin‐aniline conjugate with phosphorus(V). As a result of complexation with phosphorus, the water solubility of the porphyrin‐aniline conjugate was improved 100‐fold. Furthermore, this complexation strongly suppressed the singlet‐oxygen‐generating activity of the porphyrin photosensitizer under basic conditions, and the quantum yield of the singlet oxygen photosensitization markedly increased under acidic conditions. Based on these improvements, an extremely high ON/OFF switching ratio of the quantum yield was obtained (>400‐fold).

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