{"title":"一种氮杂环戊烯在 1,2-二氯乙烷中的光化学质子化反应","authors":"","doi":"10.1016/j.jphotochem.2024.116106","DOIUrl":null,"url":null,"abstract":"<div><div>Heterocyclic analogues of phenanthridine are an important class of nitrogen-containing compounds with promising optical properties including high quantum yield of luminescence, high molar absorption coefficients and sensitivity to solvent medium. The luminescent properties of phenanthridine and its derivatives can be changed by introducing appropriate substituents into various positions of the phenanthridine framework. Recently developed luminescent azahelicenes of furoquinoline series demonstrate strong acidochromic effect both on absorption and emission spectra. One of the features of these compounds is the photochemical formation of a protonated form in chlorine-containing solvents under UV irradiation. In this work we perform a mechanistic study of 3-methoxy-6-(4-methoxyphenyl)naphtho[1′,2′:4,5]furo[2,3-<em>c</em>]quinoline (compound <strong>1</strong>) in 1,2-dichloroethane (1,2-DCE) by means of stationary and laser flash photolysis. In addition to the triplet state formation observed in typical organic solvents photoexcitation in 1,2-DCE was found to result in an electron transfer from the excited compound <strong>1</strong> to a solvent molecule. Reactions of resulting intermediates lead to the formation of the protonated azahelicene. The quantitative mechanism of photoprotonation is put forward.</div></div>","PeriodicalId":16782,"journal":{"name":"Journal of Photochemistry and Photobiology A-chemistry","volume":null,"pages":null},"PeriodicalIF":4.1000,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photochemical protonation of an azahelicene in 1,2-dichloroethane\",\"authors\":\"\",\"doi\":\"10.1016/j.jphotochem.2024.116106\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Heterocyclic analogues of phenanthridine are an important class of nitrogen-containing compounds with promising optical properties including high quantum yield of luminescence, high molar absorption coefficients and sensitivity to solvent medium. The luminescent properties of phenanthridine and its derivatives can be changed by introducing appropriate substituents into various positions of the phenanthridine framework. Recently developed luminescent azahelicenes of furoquinoline series demonstrate strong acidochromic effect both on absorption and emission spectra. One of the features of these compounds is the photochemical formation of a protonated form in chlorine-containing solvents under UV irradiation. In this work we perform a mechanistic study of 3-methoxy-6-(4-methoxyphenyl)naphtho[1′,2′:4,5]furo[2,3-<em>c</em>]quinoline (compound <strong>1</strong>) in 1,2-dichloroethane (1,2-DCE) by means of stationary and laser flash photolysis. In addition to the triplet state formation observed in typical organic solvents photoexcitation in 1,2-DCE was found to result in an electron transfer from the excited compound <strong>1</strong> to a solvent molecule. Reactions of resulting intermediates lead to the formation of the protonated azahelicene. The quantitative mechanism of photoprotonation is put forward.</div></div>\",\"PeriodicalId\":16782,\"journal\":{\"name\":\"Journal of Photochemistry and Photobiology A-chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.1000,\"publicationDate\":\"2024-10-20\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"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/S1010603024006506\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Photochemistry and Photobiology A-chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1010603024006506","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
Photochemical protonation of an azahelicene in 1,2-dichloroethane
Heterocyclic analogues of phenanthridine are an important class of nitrogen-containing compounds with promising optical properties including high quantum yield of luminescence, high molar absorption coefficients and sensitivity to solvent medium. The luminescent properties of phenanthridine and its derivatives can be changed by introducing appropriate substituents into various positions of the phenanthridine framework. Recently developed luminescent azahelicenes of furoquinoline series demonstrate strong acidochromic effect both on absorption and emission spectra. One of the features of these compounds is the photochemical formation of a protonated form in chlorine-containing solvents under UV irradiation. In this work we perform a mechanistic study of 3-methoxy-6-(4-methoxyphenyl)naphtho[1′,2′:4,5]furo[2,3-c]quinoline (compound 1) in 1,2-dichloroethane (1,2-DCE) by means of stationary and laser flash photolysis. In addition to the triplet state formation observed in typical organic solvents photoexcitation in 1,2-DCE was found to result in an electron transfer from the excited compound 1 to a solvent molecule. Reactions of resulting intermediates lead to the formation of the protonated azahelicene. The quantitative mechanism of photoprotonation is put forward.
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.