Bicyclic 2-Pyridone, with Fused Heterocyclic Rings, a Facile Core for Pure Type I Photosensitizers

Abstract

Effectively improving the ability of electron transfer is the cornerstone of designing pure type I photosensitizers (PSs). At present, the bright strategies are to introduce the electron-rich structures to promote electron transfer capacity. Herein, we developed a novel core with fused heterocyclic ring (bicyclic 2-pyridone, BCP) based on which a series of excellent pure type I PSs can subsequently be constructed. BCP, with the fused heterocyclic rings, can act as an “electronic pool” for forming electron-rich environment. Electrochemical experiments and theoretical calculations prove that BCP has a more significant electron transfer phenomenon compared to the non-conjugated one. Based on BCP, the pure type I PSs core, triphenylamine (electron donor, D) was introduced to produce a molecule (BCP-TPA) with near infrared emission and high type I PDT efficiency by the typical D-π-D structure. BCP-TPA showed superior ability to produce pure type I ROS, which effectively inhibited tumor growth in in vivo experiments. This work provides a new core to synthesize pure type I PSs, combining fused heterocyclic rings to form electron-rich environment.

Supplementary files

Article information

Article type
Research Article
Submitted
24 Apr 2025
Accepted
08 Jun 2025
First published
12 Jun 2025

Org. Chem. Front., 2025, Accepted Manuscript

Bicyclic 2-Pyridone, with Fused Heterocyclic Rings, a Facile Core for Pure Type I Photosensitizers

Z. Ban, N. Ma, H. Tang, X. Ran, Q. Zhou, Y. Zhang, Z. Wang and X. Yu, Org. Chem. Front., 2025, Accepted Manuscript , DOI: 10.1039/D5QO00684H

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