Yuriy A. Kvashnin , Ekaterina F. Zhilina , Alyona I. Dubovik , Denis A. Gazizov , Alexandr V. Mekhaev , Elizaveta M. Krynina , Gennady L. Rusinov , Egor V. Verbitskiy , Valery N. Charushin
{"title":"将四苯基乙烯取代的噁二唑并[3,4-b]吡嗪转化为相应的咪唑并[4,5-b]吡嗪和吡嗪并[2,3-b]吡嗪,作为选择性检测水介质中硝基芳烃的化学传感器","authors":"Yuriy A. Kvashnin , Ekaterina F. Zhilina , Alyona I. Dubovik , Denis A. Gazizov , Alexandr V. Mekhaev , Elizaveta M. Krynina , Gennady L. Rusinov , Egor V. Verbitskiy , Valery N. Charushin","doi":"10.1016/j.dyepig.2024.112253","DOIUrl":null,"url":null,"abstract":"<div><p>Novel tetraphenylethylene-substituted [1,2,5]oxadiazolo[3,4-<em>b</em>]pyrazines have been synthesized, and their ability to be transformed into other annulated pyrazines in good yields has been demonstrated. The photophysical properties of all new fluorophores have been investigated, by using both absorption and emission spectral analyses in MeCN solutions and solid-state. All fluorophores proved to possess very low absolute quantum yields in solutions and absolute quantum yields up to 0.06 in solid-state, depending on their azine parts. The incorporation of tetraphenylethylene unit in the backbone endows the fluorophore a significant aggregation induced emission behavior. It has been demonstrated that novel tetraphenylethylene-substituted pyrazino[2,3-<em>b</em>]pyrazines can be used as aggregation induced emission active probes for the effective detection of nitroaromatics in solutions with a high selectivity, a high sensitivity and a fast response. On the basis of the experimental data and DFT calculations, it has been shown that a static mechanism of fluorescence quenching with a significant contribution of dynamic components takes place in case of new fluorophores. This research provides new insights into the rational design of aggregation induced emission fluorophores based on azaheterocyclic push-pull systems exploited for sensing applications.</p></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":null,"pages":null},"PeriodicalIF":4.1000,"publicationDate":"2024-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Conversion of tetraphenylethylene-substituted oxadiazolo[3,4-b]pyrazines into the corresponding imidazo[4,5-b]- and pyrazino[2,3-b]pyrazines, as chemosensors for the selective detection of nitroaromatics in aqueous media\",\"authors\":\"Yuriy A. Kvashnin , Ekaterina F. Zhilina , Alyona I. Dubovik , Denis A. Gazizov , Alexandr V. Mekhaev , Elizaveta M. Krynina , Gennady L. Rusinov , Egor V. Verbitskiy , Valery N. Charushin\",\"doi\":\"10.1016/j.dyepig.2024.112253\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Novel tetraphenylethylene-substituted [1,2,5]oxadiazolo[3,4-<em>b</em>]pyrazines have been synthesized, and their ability to be transformed into other annulated pyrazines in good yields has been demonstrated. The photophysical properties of all new fluorophores have been investigated, by using both absorption and emission spectral analyses in MeCN solutions and solid-state. All fluorophores proved to possess very low absolute quantum yields in solutions and absolute quantum yields up to 0.06 in solid-state, depending on their azine parts. The incorporation of tetraphenylethylene unit in the backbone endows the fluorophore a significant aggregation induced emission behavior. It has been demonstrated that novel tetraphenylethylene-substituted pyrazino[2,3-<em>b</em>]pyrazines can be used as aggregation induced emission active probes for the effective detection of nitroaromatics in solutions with a high selectivity, a high sensitivity and a fast response. On the basis of the experimental data and DFT calculations, it has been shown that a static mechanism of fluorescence quenching with a significant contribution of dynamic components takes place in case of new fluorophores. This research provides new insights into the rational design of aggregation induced emission fluorophores based on azaheterocyclic push-pull systems exploited for sensing applications.</p></div>\",\"PeriodicalId\":302,\"journal\":{\"name\":\"Dyes and Pigments\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.1000,\"publicationDate\":\"2024-06-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Dyes and Pigments\",\"FirstCategoryId\":\"88\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0143720824003188\",\"RegionNum\":3,\"RegionCategory\":\"工程技术\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, APPLIED\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Dyes and Pigments","FirstCategoryId":"88","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0143720824003188","RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
Conversion of tetraphenylethylene-substituted oxadiazolo[3,4-b]pyrazines into the corresponding imidazo[4,5-b]- and pyrazino[2,3-b]pyrazines, as chemosensors for the selective detection of nitroaromatics in aqueous media
Novel tetraphenylethylene-substituted [1,2,5]oxadiazolo[3,4-b]pyrazines have been synthesized, and their ability to be transformed into other annulated pyrazines in good yields has been demonstrated. The photophysical properties of all new fluorophores have been investigated, by using both absorption and emission spectral analyses in MeCN solutions and solid-state. All fluorophores proved to possess very low absolute quantum yields in solutions and absolute quantum yields up to 0.06 in solid-state, depending on their azine parts. The incorporation of tetraphenylethylene unit in the backbone endows the fluorophore a significant aggregation induced emission behavior. It has been demonstrated that novel tetraphenylethylene-substituted pyrazino[2,3-b]pyrazines can be used as aggregation induced emission active probes for the effective detection of nitroaromatics in solutions with a high selectivity, a high sensitivity and a fast response. On the basis of the experimental data and DFT calculations, it has been shown that a static mechanism of fluorescence quenching with a significant contribution of dynamic components takes place in case of new fluorophores. This research provides new insights into the rational design of aggregation induced emission fluorophores based on azaheterocyclic push-pull systems exploited for sensing applications.
期刊介绍:
Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied.
Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media.
The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.