Synthesis and properties of novel type I photosensitizer polycyclic amide

Kui Wang; Tao Ye; Haoyang Du; Xiangyu Jin; Xiaofen Yi; Huiying Gao; Yuan Zhang; Wei Dong; Shihui Liu; Jing Guan; Feng Lin; Debin Xia

doi:10.1039/d3na00341h

Synthesis and properties of novel type I photosensitizer polycyclic amide

Nanoscale Adv. 2023 Jun 29;5(14):3629-3633. doi: 10.1039/d3na00341h. eCollection 2023 Jul 11.

Authors

Kui Wang¹, Tao Ye¹, Haoyang Du¹, Xiangyu Jin¹, Xiaofen Yi¹, Huiying Gao¹, Yuan Zhang¹, Wei Dong¹, Shihui Liu², Jing Guan¹, Feng Lin¹, Debin Xia^{2

3}

Affiliations

¹ Department of Organic Chemistry, College of Pharmacy, Harbin Medical University Harbin China guanjing@ems.hrbmu.edu.cn xiaolin_linfeng@126.com.
² MIIT Key Laboratory of Critical Materials Technology for New Energy Conversion and Storage, School of Chemistry and Chemical Engineering, Harbin Institute of Technology Harbin China.
³ State Key Laboratory of Urban Water Resource and Environment, Harbin Institute of Technology Harbin China.

Abstract

Herein, we have designed and synthesized a novel type-I photosensitizer (PhPA) via Rh-catalyzed oxidative cyclization of diacetoxyterephthalamide with alkynes. The photoelectric properties, photosensitivity and photodegradation process of PhPA have been systematically investigated. The remarkable fluorescence quenching effect (Φ_PL < 0.01) of PhPA suggests that the intersystem crossing from the singlet excited state to the reactive triplet state is enhanced by the enlarged conjugated backbone. Additionally, the ability of superoxide radical (O₂^-˙) generation was confirmed by electron paramagnetic resonance spectroscopy. Finally, the mechanism of PhPA photo-oxidative degradation via the structure of two metabolites is proposed.