Conjugation-regulating synthesis of high photosensitizing activity porphyrin-based covalent organic frameworks for photodynamic inactivation of bacteria

IF 6.1 1区化学 Q1 CHEMISTRY, ANALYTICAL

Talanta Pub Date : 2021-10-01 DOI:10.1016/j.talanta.2021.122536

Fan-Lin Meng , Hai-Long Qian , Xiu-Ping Yan

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引用次数: 8

Abstract

Preparation of porphyrin-based covalent organic frameworks (Por-COFs) with high photosensitizing activity for photodynamic inactivation of bacteria is of great challenge, but significant for economy and human health. Herein, we show a conjugation-regulating strategy to design and synthesize Por-COFs with high photosensitizing activity for the photodynamic inactivation of bacteria. Terephthalaldehyde (Da), 2,5-Dihydroxyterephthalaldehyde (Dha), and 2,5-Diethoxyterephthalaldehyde (Deta) with different conjugation degrees are selected to condense with 5,10,15,20-Tetrakis(4-aminophenyl)porphyrin (Tph) to synthesize COF-366, DhaTph, and JNU-2, respectively. The higher conjugation of Dha and Deta than Da leads to the higher conjugation of DhaTph and JNU-2, respectively. Moreover, the hydroxyl group in Dha and the ethoxy group in Deta further expand the conjugation of DhaTph and JNU-2 via the formation of intralayer extended π-cloud delocalization and p-π conjunction, respectively. The extension of conjugation for DhaTph and JNU-2 results in the increase of intersystem crossing process and significantly improves their photosensitizing activity. Furthermore, JNU-2 with the highest photosensitizing activity exhibits superior antibacterial effects toward Staphylococcus aureus (99.1%) and Escherichia coli (96.8%). This study offers a new conjugation-regulating strategy for designing high photosensitizing activity of Por-COFs for the inactivation of bacteria.

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高光敏活性卟啉共价有机框架的偶联调控合成及其对细菌光动力失活的影响

制备具有高光敏活性的卟啉基共价有机框架(Por-COFs)用于细菌光动力灭活是一项巨大的挑战，但对经济和人类健康具有重要意义。在此，我们展示了一种偶联调节策略来设计和合成具有高光敏活性的Por-COFs，用于细菌的光动力失活。选择不同共轭度的对苯二甲酸(Da)、2,5-二羟基对苯二甲酸(Dha)和2,5-二氧基对苯二甲酸(Deta)分别与5,10,15,20-四(4-氨基苯基)卟啉(Tph)缩合，合成COF-366、DhaTph和JNU-2。Dha和Deta的共轭性比Da高，分别导致DhaTph和JNU-2的共轭性更高。此外，Dha中的羟基和Deta中的乙氧基分别通过层内扩展π-云离域和p-π连接进一步扩大了DhaTph和JNU-2的偶联。DhaTph和JNU-2偶联的扩展导致系统间杂交过程增加，光敏活性显著提高。此外，光敏活性最高的JNU-2对金黄色葡萄球菌(99.1%)和大肠杆菌(96.8%)的抑菌效果也较好。本研究为设计高光敏活性的Por-COFs灭活细菌提供了一种新的偶联调控策略。

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来源期刊

Talanta 化学-分析化学

CiteScore

12.30

自引率

4.90%

发文量

861

审稿时长

29 days

期刊介绍： Talanta provides a forum for the publication of original research papers, short communications, and critical reviews in all branches of pure and applied analytical chemistry. Papers are evaluated based on established guidelines, including the fundamental nature of the study, scientific novelty, substantial improvement or advantage over existing technology or methods, and demonstrated analytical applicability. Original research papers on fundamental studies, and on novel sensor and instrumentation developments, are encouraged. Novel or improved applications in areas such as clinical and biological chemistry, environmental analysis, geochemistry, materials science and engineering, and analytical platforms for omics development are welcome. Analytical performance of methods should be determined, including interference and matrix effects, and methods should be validated by comparison with a standard method, or analysis of a certified reference material. Simple spiking recoveries may not be sufficient. The developed method should especially comprise information on selectivity, sensitivity, detection limits, accuracy, and reliability. However, applying official validation or robustness studies to a routine method or technique does not necessarily constitute novelty. Proper statistical treatment of the data should be provided. Relevant literature should be cited, including related publications by the authors, and authors should discuss how their proposed methodology compares with previously reported methods.