文献类型：期刊文献

英文题名：Modulating the Luminescence, Photosensitizing Properties, and Mitochondria-Targeting Ability of D-p-A-Structured Dihydrodibenzo[a,c]phenazines

作者：Zhang, Zhaozhi[1];Wang, Qijing[1];Zhang, Xinyi[1];Mei, Dong[2];Mei, Ju[1]

机构：[1]East China Univ Sci & Technol, Joint Int Res Lab Precis Chem & Mol Engn, Frontiers Sci Ctr Materiobiol & Dynam Chem, Sch Chem & Mol Engn,Inst Fine Chem,Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]Capital Med Univ, Beijing Childrens Hosp, Clin Res Ctr, Natl Ctr Childrens Hlth, Beijing 100045, Peoples R China

年份：2023

卷号：28

期号：17

外文期刊名：MOLECULES

收录：;WOS:【SCI-EXPANDED(收录号:WOS:001064117300001)】；

基金：The authors thank the Research Center of Analysis and Test of East China University of Science and Technology for the help on the characterization.

语种：英文

外文关键词：aggregation-induced emission; vibration-induced emission; photodynamic therapy; mitochondria-specific imaging; photosensitizing properties; dihydrodibenzo[a,c]phenazines

摘要：Herein, pyridinium and 4-vinylpyridinium groups are introduced into the VIE-active N,N'-disubstituted-dihydrodibenzo[a,c]phenazines (DPAC) framework to afford a series of D -p-A structured dihydrodibenzo[a,c]phenazines in consideration of the aggregation-benefited performance of the DPAC module and the potential mitochondria-targeting capability of the resultant pyridiniumdecorated DPACs (DPAC-PyPF(6)and DPAC-D-PyPF6). To modulate the properties and elucidate the structure-property relationship, the corresponding pyridinyl/4-vinylpyridinyl-substituted DPACs, i.e., DPAC-Py and DPAC-D-Py, are designed and studied as controls. It is found that the strong intramolecular charge transfer (ICT) effect enables the effective separation of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of DPAC-PyPF(6)and DPAC-D-PyPF6, which is conducive to the generation of ROS. By adjusting the electron-accepting group and the p-bridge, the excitation, absorption, luminescence, photosensitizing properties as well as the mitochondria-targeting ability can be finely tuned. Both DPAC-PyPF(6)and DPAC-D-PyPF(6)display large Stokes shifts (70-222 nm), solvent-dependent absorptions and emissions, aggregation induced emission (AIE), red fluorescence in the aggregated state (?(em) = 600-650 nm), aggregation promoted photosensitizing ability with the relative singlet-oxygen quantum yields higher than 1.10, and a mitochondria-targeting ability with the Pearson coefficients larger than 0.85. DPAC-D-PyPF(6)shows absorption maximum at a longer wavelength, slightly redder fluorescence and better photosensitivity as compared to DPAC-PyPF6, which consequently leads to the higher photocytotoxicity under the irradiation of white light as a result of the larger Tr-conjugation.