Near-infrared red (NIR) fluorescence imaging guide phototherapeutic therapy (PDT) has the advantages of deep tissue penetration, real-time monitoring of drug treatment and disease, little damage to normal tissue, low cytotoxicity and almost no side effects, and thus, it is attracting increasing research attention and is expected to show promising potential for clinical tumor treatment. The photosensitizer (PS), light source and oxygen are the three basic and important factors to construct PDT technology, and highly efficient PSs are still being passionately pursued because they determine the PDT efficiency. Ideal PSs should have properties such as good biocompatibility, deep tissue penetration, and highly efficient reactive oxygen species (ROS) generation despite the hypoxic environment. Therefore, pure organic type I PSs with NIR fluorescence have been receiving increasing attention due to their deep penetration and hypoxia resistance. However, reported NIR-active type I PSs usually require complex synthetic procedures, which presents a challenge for mass production. In this research work, based on the molecular design ideas of introducing the heavy atom effect and intramolecular charge transfer, we prepared three NIR-active type I PSs (TNZ, TNZBr, and TNZCHO) using a very simple method with one or two synthetic steps. Clear characterizations of photophysical properties, ROS performance tests, and fluorescent imaging of human umbilical vein endothelial (HUVE) cells and PDT treatment of HepG2 cells were carried out. The results revealed that the heavy atom and intramolecular charge transfer (ICT) effects could obviously enhance the ROS efficiency, and both PSs produce only type I ROS without any type II ROS (1O2) generation. The good NIR fluorescence brightness and type I ROS efficiency ensure satisfactory bioimaging and PDT outcomes. This research provides the possibility of preparing NIR-active type I PSs via mass production.
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