{"title":"Substituent effects on the ESIPT process of H2O2 sensing product 1,3-bis(bispyridin-2-ylimino) isoindolin-4-ol: A theoretical study","authors":"","doi":"10.1016/j.jphotochem.2024.115966","DOIUrl":null,"url":null,"abstract":"<div><p>H<sub>2</sub>O<sub>2</sub> plays an important role in a variety of physiological processes, but its overproduction or accumulation can lead to oxidative damage and related diseases, so it is crucial to establish accurate H<sub>2</sub>O<sub>2</sub> detection methods. Fluorescence sensing as a potential method, the design and modulation of its luminescent properties are crucial to the detection results. In this work, we investigated the sensing mechanism of a novel H<sub>2</sub>O<sub>2</sub> fluorescent probe (P1) and examined the role of substituent effects in modulating the fluorescence properties of its reaction products. The results show that the non-fluorescence property of the probe is due to twisted intramolecular charge transfer (TICT) mechanism resulting from a torsion of the excited state molecular conformation, and the fluorescence turn-on upon recognition of H<sub>2</sub>O<sub>2</sub> by the probe is due to the reaction product (BBYI1) following the excited state intramolecular proton transfer (ESIPT) process. When the substituent is an electron-donating group, the energy barrier of the ESIPT reaction is lowered, promoting luminescence, while the electron-withdrawing group has the opposite effect. In summary, the present work may offer a theoretical foundation for the development of more sensitive fluorescent probes for ESIPT-based H<sub>2</sub>O<sub>2</sub> detection.</p></div>","PeriodicalId":16782,"journal":{"name":"Journal of Photochemistry and Photobiology A-chemistry","volume":null,"pages":null},"PeriodicalIF":4.1000,"publicationDate":"2024-08-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S1010603024005100/pdfft?md5=ca069a9322d612c0f8abcb1f96622434&pid=1-s2.0-S1010603024005100-main.pdf","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Photochemistry and Photobiology A-chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1010603024005100","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0
Abstract
H2O2 plays an important role in a variety of physiological processes, but its overproduction or accumulation can lead to oxidative damage and related diseases, so it is crucial to establish accurate H2O2 detection methods. Fluorescence sensing as a potential method, the design and modulation of its luminescent properties are crucial to the detection results. In this work, we investigated the sensing mechanism of a novel H2O2 fluorescent probe (P1) and examined the role of substituent effects in modulating the fluorescence properties of its reaction products. The results show that the non-fluorescence property of the probe is due to twisted intramolecular charge transfer (TICT) mechanism resulting from a torsion of the excited state molecular conformation, and the fluorescence turn-on upon recognition of H2O2 by the probe is due to the reaction product (BBYI1) following the excited state intramolecular proton transfer (ESIPT) process. When the substituent is an electron-donating group, the energy barrier of the ESIPT reaction is lowered, promoting luminescence, while the electron-withdrawing group has the opposite effect. In summary, the present work may offer a theoretical foundation for the development of more sensitive fluorescent probes for ESIPT-based H2O2 detection.
期刊介绍:
JPPA publishes the results of fundamental studies on all aspects of chemical phenomena induced by interactions between light and molecules/matter of all kinds.
All systems capable of being described at the molecular or integrated multimolecular level are appropriate for the journal. This includes all molecular chemical species as well as biomolecular, supramolecular, polymer and other macromolecular systems, as well as solid state photochemistry. In addition, the journal publishes studies of semiconductor and other photoactive organic and inorganic materials, photocatalysis (organic, inorganic, supramolecular and superconductor).
The scope includes condensed and gas phase photochemistry, as well as synchrotron radiation chemistry. A broad range of processes and techniques in photochemistry are covered such as light induced energy, electron and proton transfer; nonlinear photochemical behavior; mechanistic investigation of photochemical reactions and identification of the products of photochemical reactions; quantum yield determinations and measurements of rate constants for primary and secondary photochemical processes; steady-state and time-resolved emission, ultrafast spectroscopic methods, single molecule spectroscopy, time resolved X-ray diffraction, luminescence microscopy, and scattering spectroscopy applied to photochemistry. Papers in emerging and applied areas such as luminescent sensors, electroluminescence, solar energy conversion, atmospheric photochemistry, environmental remediation, and related photocatalytic chemistry are also welcome.