TY - JOUR
T1 - Peripheral RAFT Polymerization on a Covalent Organic Polymer with Enhanced Aqueous Compatibility for Controlled Generation of Singlet Oxygen
AU - Lai, Haiwang
AU - Yan, Jieyu
AU - Liu, Shan
AU - Yang, Qizhi
AU - Xing, Feiyue
AU - Xiao, Pu
N1 - Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2020/6/22
Y1 - 2020/6/22
N2 - A covalent organic polymer (COP) is prepared by crosslinking the photosensitizer 4,4′,4′′,4′′′-(porphyrin-5,10,15,20-tetrayl)tetraaniline (TAPP) with 4,4′-(anthracene-9,10-diyl)dibenzoic acid (ADDA) via 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide/4-dimethylaminopyridine coupling. The COP is further modified with a hydrophilic polymer, poly(poly(ethylene glycol) methyl ether methacrylate) by grafting-from reversible-addition-fragmentation chain transfer (RAFT) polymerization to enhance its solubility in various solvents. The modified COP can bind singlet oxygen through the formation of endoperoxide by ADDA upon the exposure to red light irradiation. Singlet oxygen can be then released via the photodynamic mechanism or the cycloreversion by endoperoxide when heated at 110 °C. These results open new possibilities for simultaneous generation of singlet oxygen by the photodynamic route and singlet oxygen carriers, demonstrating promise for treating hypoxic tumors.
AB - A covalent organic polymer (COP) is prepared by crosslinking the photosensitizer 4,4′,4′′,4′′′-(porphyrin-5,10,15,20-tetrayl)tetraaniline (TAPP) with 4,4′-(anthracene-9,10-diyl)dibenzoic acid (ADDA) via 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide/4-dimethylaminopyridine coupling. The COP is further modified with a hydrophilic polymer, poly(poly(ethylene glycol) methyl ether methacrylate) by grafting-from reversible-addition-fragmentation chain transfer (RAFT) polymerization to enhance its solubility in various solvents. The modified COP can bind singlet oxygen through the formation of endoperoxide by ADDA upon the exposure to red light irradiation. Singlet oxygen can be then released via the photodynamic mechanism or the cycloreversion by endoperoxide when heated at 110 °C. These results open new possibilities for simultaneous generation of singlet oxygen by the photodynamic route and singlet oxygen carriers, demonstrating promise for treating hypoxic tumors.
KW - covalent organic polymers
KW - endoperoxides
KW - grafting-from
KW - photodynamic mechanism
KW - singlet oxygen
UR - http://www.scopus.com/inward/record.url?scp=85082954601&partnerID=8YFLogxK
U2 - 10.1002/anie.202002446
DO - 10.1002/anie.202002446
M3 - Article
SN - 1433-7851
VL - 59
SP - 10431
EP - 10435
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 26
ER -