Water-Soluble Single-Benzene Chromophores: Excited State Dynamics and Fluorescence Detection
Two water-soluble single-benzene-based chromophores, 2,5-di(azetidine-1-yl)-tereph- thalic acid (<b>DAPA</b>) and its disodium carboxylate (<b>DAP-Na</b>), were conveniently obtained. Both chromophores preserved moderate quantum yields in a wide range of polar and protonic so...
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MDPI AG
2022-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/17/5522 |
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| author | Yingge Fan Jin Ma Huijing Liu Taihong Liu |
| author_facet | Yingge Fan Jin Ma Huijing Liu Taihong Liu |
| author_sort | Yingge Fan |
| collection | DOAJ |
| description | Two water-soluble single-benzene-based chromophores, 2,5-di(azetidine-1-yl)-tereph- thalic acid (<b>DAPA</b>) and its disodium carboxylate (<b>DAP-Na</b>), were conveniently obtained. Both chromophores preserved moderate quantum yields in a wide range of polar and protonic solvents. Spectroscopic studies demonstrated that <b>DAPA</b> exhibited red luminescence as well as large Stokes shift (>200 nm) in aqueous solutions. Femtosecond transient absorption spectra illustrated quadrupolar <b>DAPA</b> usually involved the formation of an intramolecular charge transfer state. Its Frank–Condon state could be rapidly relaxed to a slight symmetry-breaking state upon light excitation following the solvent relaxation, then the slight charge separation may occur and the charge localization became partially asymmetrical in polar environments. Density functional theory (DFT) calculation results were supported well with the experimental measurements. Unique pH-dependent fluorescent properties endows the two chromophores with rapid, highly selective, and sensitive responses to the amino acids in aqueous media. In detail, <b>DAPA</b> served as a fluorescence turn-on probe with a detection limit (DL) of 0.50 μM for Arg and with that of 0.41 μM for Lys. In contrast, <b>DAP-Na</b> featured bright green luminescence and showed fluorescence turn-off responses to Asp and Glu with the DLs of 0.12 μM and 0.16 μM, respectively. Meanwhile, these two simple-structure probes exhibited strong anti-interference ability towards other natural amino acids and realized visual identification of specific analytes. The present work helps to understand the photophysic–structure relationship of these kinds of compounds and render their fluorescent detection applications. |
| first_indexed | 2024-03-10T01:30:35Z |
| format | Article |
| id | doaj.art-5d9d7435b3364bb5bfd7dc63ac2a756e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T01:30:35Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj.art-5d9d7435b3364bb5bfd7dc63ac2a756e2023-11-23T13:43:25ZengMDPI AGMolecules1420-30492022-08-012717552210.3390/molecules27175522Water-Soluble Single-Benzene Chromophores: Excited State Dynamics and Fluorescence DetectionYingge Fan0Jin Ma1Huijing Liu2Taihong Liu3Department of Chemical Engineering, Shaanxi Institute of Technology, Xi’an 710300, ChinaDepartment of Chemical Engineering, Shaanxi Institute of Technology, Xi’an 710300, ChinaKey Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, ChinaKey Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, ChinaTwo water-soluble single-benzene-based chromophores, 2,5-di(azetidine-1-yl)-tereph- thalic acid (<b>DAPA</b>) and its disodium carboxylate (<b>DAP-Na</b>), were conveniently obtained. Both chromophores preserved moderate quantum yields in a wide range of polar and protonic solvents. Spectroscopic studies demonstrated that <b>DAPA</b> exhibited red luminescence as well as large Stokes shift (>200 nm) in aqueous solutions. Femtosecond transient absorption spectra illustrated quadrupolar <b>DAPA</b> usually involved the formation of an intramolecular charge transfer state. Its Frank–Condon state could be rapidly relaxed to a slight symmetry-breaking state upon light excitation following the solvent relaxation, then the slight charge separation may occur and the charge localization became partially asymmetrical in polar environments. Density functional theory (DFT) calculation results were supported well with the experimental measurements. Unique pH-dependent fluorescent properties endows the two chromophores with rapid, highly selective, and sensitive responses to the amino acids in aqueous media. In detail, <b>DAPA</b> served as a fluorescence turn-on probe with a detection limit (DL) of 0.50 μM for Arg and with that of 0.41 μM for Lys. In contrast, <b>DAP-Na</b> featured bright green luminescence and showed fluorescence turn-off responses to Asp and Glu with the DLs of 0.12 μM and 0.16 μM, respectively. Meanwhile, these two simple-structure probes exhibited strong anti-interference ability towards other natural amino acids and realized visual identification of specific analytes. The present work helps to understand the photophysic–structure relationship of these kinds of compounds and render their fluorescent detection applications.https://www.mdpi.com/1420-3049/27/17/5522single-benzene chromophorefemtosecond transient absorptionexcited state dynamicfluorescence detectionvisual identification |
| spellingShingle | Yingge Fan Jin Ma Huijing Liu Taihong Liu Water-Soluble Single-Benzene Chromophores: Excited State Dynamics and Fluorescence Detection Molecules single-benzene chromophore femtosecond transient absorption excited state dynamic fluorescence detection visual identification |
| title | Water-Soluble Single-Benzene Chromophores: Excited State Dynamics and Fluorescence Detection |
| title_full | Water-Soluble Single-Benzene Chromophores: Excited State Dynamics and Fluorescence Detection |
| title_fullStr | Water-Soluble Single-Benzene Chromophores: Excited State Dynamics and Fluorescence Detection |
| title_full_unstemmed | Water-Soluble Single-Benzene Chromophores: Excited State Dynamics and Fluorescence Detection |
| title_short | Water-Soluble Single-Benzene Chromophores: Excited State Dynamics and Fluorescence Detection |
| title_sort | water soluble single benzene chromophores excited state dynamics and fluorescence detection |
| topic | single-benzene chromophore femtosecond transient absorption excited state dynamic fluorescence detection visual identification |
| url | https://www.mdpi.com/1420-3049/27/17/5522 |
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