Construction of Photosensitizer Candidates in Photodynamic Therapy: Computer Aided Design, Calculation, and Screening

IF 3.3 2区 化学 Q1 CHEMISTRY, ORGANIC Journal of Organic Chemistry Pub Date : 2025-01-29 DOI:10.1021/acs.joc.4c02428
Wei-Huang Yin, Yang Liu, Hou-Hou Huang, Peng-Yuan Li, Xin Liu, Fu-Quan Bai
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Abstract

Thiophene and pyrrole units are extensively utilized in light-responsive materials and have significantly advanced the field of organic photovoltaics (OPV). This progress has inspired our exploration of photosensitizers (PS) for photodynamic therapy (PDT). Currently, traditional PS face limitations in clinical application, including a restricted variety and narrow applicability. Drawing upon molecular design concepts from OPV, we aim to transcend these limitations in PDT. Given the abundance of candidate molecules, effective screening is crucial. Theoretical calculations and electronic structure analyses serve as precise and practical screening methods. In this study, we adopted strategies successfully employed in OPV molecular design, focusing on donor–acceptor (D-A) and acceptor–donor–acceptor (A-D-A) structures. Using density functional theory (DFT) and time-dependent density functional theory (TDDFT), we systematically designed combinations of promising organic fragments. These fragments include polythiophene and polypyrrole-dominated donor structures, paired with five electron acceptors: indene (Ind), diketopyrrole (DPP), naphthalimide (Ni), benzothiazole (Btd), and dithiazolyl diketopyrrole (Tbo). Through meticulous calculations, we obtained electronic structures and spectral properties for all candidate molecules, facilitating an efficient screening process. Our findings highlight that those combinations of polypyrrole-based frameworks with DPP, Ni, and Btd show significant promise for PS applications. Approximately 13% of candidates were selected through comprehensive comparison, markedly reducing molecular design time and experimental costs. This interdisciplinary approach holds potential to pave the way for more targeted and successful PS designs.

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来源期刊
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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