Peripheral RAFT Polymerization on a Covalent Organic Polymer with Enhanced Aqueous Compatibility for Controlled Generation of Singlet Oxygen.,Angewandte Chemie International Edition

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Peripheral RAFT Polymerization on a Covalent Organic Polymer with Enhanced Aqueous Compatibility for Controlled Generation of Singlet Oxygen.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-03-20 , DOI: 10.1002/anie.202002446
Haiwang Lai _{1,

2} , Jieyu Yan ₁ , Shan Liu ₁ , Qizhi Yang ₁ , Feiyue Xing _{1,

3} , Pu Xiao ₂

Affiliation

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.

中文翻译：

在具有增强的水相容性的共价有机聚合物上进行外围RAFT聚合，以控制单线态氧的产生。

共价有机聚合物（COP）是通过将光敏剂4,4'，4''，4''-（卟啉-5,10,15,20-四基）四苯胺（TAPP）与4,4'- （蒽-9,10-二基）二苯甲酸（ADDA）通过1-乙基-3-（3-二甲基氨基丙基）碳二亚胺/ 4-二甲基氨基吡啶偶联。通过可逆加成-断裂链转移（RAFT）接枝反应，通过亲水性聚合物聚（聚（乙二醇）甲基醚甲基丙烯酸甲酯）对COP进行进一步改性，以提高其在各种溶剂中的溶解度。改性的COP在暴露于红光照射下可以通过ADDA形成内过氧化物而结合单线态氧。当加热到110°C时，单线态氧可以通过光动力机制或内过氧化物的环还原反应释放出来。

更新日期：2020-03-20

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