Aminoquinoxaline-Based Dual Colorimetric and Fluorescent Sensors for pH Measurement in Aqueous Media
This research is focused on the development of pH indicators based on the quinoxaline signaling group for acidic aqueous solutions (pH 1–5). A push–pull quinoxaline <b>QC1</b> in which two electron-donating (3-aminopropyl)amino substituents are attached to positions 6 and 7 of the electr...
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| Format: | Article |
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MDPI AG
2022-08-01
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| Series: | Chemosensors |
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| Online Access: | https://www.mdpi.com/2227-9040/10/8/342 |
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| author | Elizaveta V. Ermakova Andrey V. Cheprakov Alla Bessmertnykh-Lemeune |
| author_facet | Elizaveta V. Ermakova Andrey V. Cheprakov Alla Bessmertnykh-Lemeune |
| author_sort | Elizaveta V. Ermakova |
| collection | DOAJ |
| description | This research is focused on the development of pH indicators based on the quinoxaline signaling group for acidic aqueous solutions (pH 1–5). A push–pull quinoxaline <b>QC1</b> in which two electron-donating (3-aminopropyl)amino substituents are attached to positions 6 and 7 of the electron-deficient quinoxaline moiety was prepared using the palladium-catalyzed C–N cross-coupling reaction. The 3-aminopropyl residues are mostly protonated in aqueous solutions below pH 8, thus serving as hydrophilizing substituents that render quinoxaline derivative <b>QC1</b> water-soluble in this range of acidities and useful for measurements in the pH range of 1–5. This chromophore is a dual optical chemosensor that exhibits shifts of both absorption and emission bands in response to external stimuli. The presence of naturally relevant metal cations (13 ions) does not interfere with spectrophotometric and fluorescence measurements of the optical response of aminoquinoxaline in the visible region. Moreover, these spectral changes are easily observed by the naked eye, allowing for rapid semi-quantitative analyses under “in-field” conditions. |
| first_indexed | 2024-03-09T13:40:48Z |
| format | Article |
| id | doaj.art-ddcf9e5d4e7045a2968694ec6f5933c3 |
| institution | Directory Open Access Journal |
| issn | 2227-9040 |
| language | English |
| last_indexed | 2024-03-09T13:40:48Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemosensors |
| spelling | doaj.art-ddcf9e5d4e7045a2968694ec6f5933c32023-11-30T21:07:54ZengMDPI AGChemosensors2227-90402022-08-0110834210.3390/chemosensors10080342Aminoquinoxaline-Based Dual Colorimetric and Fluorescent Sensors for pH Measurement in Aqueous MediaElizaveta V. Ermakova0Andrey V. Cheprakov1Alla Bessmertnykh-Lemeune2Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky Pr. 31-4, Moscow 119071, RussiaDepartment of Chemistry, Lomonosov Moscow State University, 1-3, Leninskie Gory, Moscow 119991, RussiaInstitut de Chimie Moléculaire de l’Université de Bourgogne, CNRS UMR 6302, Université Bourgogne Franche-Comté, 9 Avenue Alain Savary, BP 47870, 21078 Dijon, FranceThis research is focused on the development of pH indicators based on the quinoxaline signaling group for acidic aqueous solutions (pH 1–5). A push–pull quinoxaline <b>QC1</b> in which two electron-donating (3-aminopropyl)amino substituents are attached to positions 6 and 7 of the electron-deficient quinoxaline moiety was prepared using the palladium-catalyzed C–N cross-coupling reaction. The 3-aminopropyl residues are mostly protonated in aqueous solutions below pH 8, thus serving as hydrophilizing substituents that render quinoxaline derivative <b>QC1</b> water-soluble in this range of acidities and useful for measurements in the pH range of 1–5. This chromophore is a dual optical chemosensor that exhibits shifts of both absorption and emission bands in response to external stimuli. The presence of naturally relevant metal cations (13 ions) does not interfere with spectrophotometric and fluorescence measurements of the optical response of aminoquinoxaline in the visible region. Moreover, these spectral changes are easily observed by the naked eye, allowing for rapid semi-quantitative analyses under “in-field” conditions.https://www.mdpi.com/2227-9040/10/8/342quinoxalinepH indicatorcolorimetryfluorescenceoptical chemosensor |
| spellingShingle | Elizaveta V. Ermakova Andrey V. Cheprakov Alla Bessmertnykh-Lemeune Aminoquinoxaline-Based Dual Colorimetric and Fluorescent Sensors for pH Measurement in Aqueous Media Chemosensors quinoxaline pH indicator colorimetry fluorescence optical chemosensor |
| title | Aminoquinoxaline-Based Dual Colorimetric and Fluorescent Sensors for pH Measurement in Aqueous Media |
| title_full | Aminoquinoxaline-Based Dual Colorimetric and Fluorescent Sensors for pH Measurement in Aqueous Media |
| title_fullStr | Aminoquinoxaline-Based Dual Colorimetric and Fluorescent Sensors for pH Measurement in Aqueous Media |
| title_full_unstemmed | Aminoquinoxaline-Based Dual Colorimetric and Fluorescent Sensors for pH Measurement in Aqueous Media |
| title_short | Aminoquinoxaline-Based Dual Colorimetric and Fluorescent Sensors for pH Measurement in Aqueous Media |
| title_sort | aminoquinoxaline based dual colorimetric and fluorescent sensors for ph measurement in aqueous media |
| topic | quinoxaline pH indicator colorimetry fluorescence optical chemosensor |
| url | https://www.mdpi.com/2227-9040/10/8/342 |
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