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Study on Five Porphyrin‐Based Photosensitizers for Singlet Oxygen Generation
Author(s) -
Zu GuoPing,
Wang JinJin,
Zhang Yan,
Chen WangBin,
Shi YuZhong,
Guo ShengWei,
Wang XiaoRong
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201803654
Subject(s) - porphyrin , singlet oxygen , photochemistry , photosensitizer , absorbance , chemistry , photodynamic therapy , absorption (acoustics) , oxygen , sunlight , singlet state , absorption spectroscopy , materials science , organic chemistry , optics , excited state , physics , chromatography , nuclear physics , composite material
Five porphyrin derivatives were synthesized and characterized in order to be utilized as photosensitizers for singlet oxygen generation. UV‐Vis absorption properties of porphyrins were experimentally and theoretically discussed. The results indicated that the increase in π‐conjugation of porphyrin core can lower the S 1 ‐T 1 energy gap and is favorable for efficient energy transfer. The singlet oxygen generation ability of porphyrins was measured and compared under both simulated sunlight and yellow light. As for the results using simulated sunlight, EBHPP and CEBHPP exhibited best and similar performance because they bear strong near‐IR absorption and S 1 ‐T 1 interactions. However, under yellow light conditions CEBHPP has better ability for singlet oxygen generation because of its strong absorbance from 650–750 nm. The DNA photocleavage measurements were performed to evaluate the biological activity of the porphyrin derivatives. The photocleavage activities were in the order of TPP < TPP‐NO 2 < BHPP < EBHPP < CEBHPP , and the possible reasons were discussed. This work is useful for the design of more efficient photosensitizers.