A Highly Water-Soluble Fluorescent and Colorimetric pH Probe
A new 5-(4-((2-(benzothiazole-2-carbonyl)hydrazono)methyl)-3-hydroxyphenoxy)-N,N,N-trimethylpentan-1-aminium bromide (BTABr) fluorescent and colorimetric pH probe was easily synthesized by the condensation reaction of benzothiazole-2-carbohydrazide with 5-(4-formyl-3-hydroxyphenoxy)-N,N,N-trimethylp...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-02-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/10/2/83 |
| _version_ | 1828283652699586560 |
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| author | Rosita Diana Ugo Caruso Angela Tuzi Barbara Panunzi |
| author_facet | Rosita Diana Ugo Caruso Angela Tuzi Barbara Panunzi |
| author_sort | Rosita Diana |
| collection | DOAJ |
| description | A new 5-(4-((2-(benzothiazole-2-carbonyl)hydrazono)methyl)-3-hydroxyphenoxy)-N,N,N-trimethylpentan-1-aminium bromide (BTABr) fluorescent and colorimetric pH probe was easily synthesized by the condensation reaction of benzothiazole-2-carbohydrazide with 5-(4-formyl-3-hydroxyphenoxy)-N,N,N-trimethylpentan-1-aminium bromide. The benzothiazole moiety provided the emissive part of the molecule and the charged trimethyl amino group guaranteed outstanding solubility in water, for an organic molecule. pH titration experiments indicated that the probe is useful for monitoring acidic and alkaline solutions, turning reversibly in color/fluorescence just at a neutral pH value. Naked-eye colorimetric response was observed both in solution and in the solid state. In addition, the probe showed high stability and selectivity and large Stokes shifts. Because of these features, BTABr can potentially work as an on-off real-time pH sensor for intracellular pH imaging. The crystal structure of BTABr examined by single-crystal analysis showed a planar geometry of the molecule and confirmed the presence of a molecular stacking between molecules joined in a complex tridimensional hydrogen bonding pattern. |
| first_indexed | 2024-04-13T08:48:50Z |
| format | Article |
| id | doaj.art-5fff497497c743ffa70777d2a25448d5 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-04-13T08:48:50Z |
| publishDate | 2020-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-5fff497497c743ffa70777d2a25448d52022-12-22T02:53:35ZengMDPI AGCrystals2073-43522020-02-011028310.3390/cryst10020083cryst10020083A Highly Water-Soluble Fluorescent and Colorimetric pH ProbeRosita Diana0Ugo Caruso1Angela Tuzi2Barbara Panunzi3Department of Agriculture, University of Napoli Federico II, 80055 Portici NA, ItalyDepartment of Chemical Sciences, University of Napoli Federico II, 80126 Napoli, ItalyDepartment of Chemical Sciences, University of Napoli Federico II, 80126 Napoli, ItalyDepartment of Agriculture, University of Napoli Federico II, 80055 Portici NA, ItalyA new 5-(4-((2-(benzothiazole-2-carbonyl)hydrazono)methyl)-3-hydroxyphenoxy)-N,N,N-trimethylpentan-1-aminium bromide (BTABr) fluorescent and colorimetric pH probe was easily synthesized by the condensation reaction of benzothiazole-2-carbohydrazide with 5-(4-formyl-3-hydroxyphenoxy)-N,N,N-trimethylpentan-1-aminium bromide. The benzothiazole moiety provided the emissive part of the molecule and the charged trimethyl amino group guaranteed outstanding solubility in water, for an organic molecule. pH titration experiments indicated that the probe is useful for monitoring acidic and alkaline solutions, turning reversibly in color/fluorescence just at a neutral pH value. Naked-eye colorimetric response was observed both in solution and in the solid state. In addition, the probe showed high stability and selectivity and large Stokes shifts. Because of these features, BTABr can potentially work as an on-off real-time pH sensor for intracellular pH imaging. The crystal structure of BTABr examined by single-crystal analysis showed a planar geometry of the molecule and confirmed the presence of a molecular stacking between molecules joined in a complex tridimensional hydrogen bonding pattern.https://www.mdpi.com/2073-4352/10/2/83ph sensorbenzothiazolewater solublefluorescence |
| spellingShingle | Rosita Diana Ugo Caruso Angela Tuzi Barbara Panunzi A Highly Water-Soluble Fluorescent and Colorimetric pH Probe Crystals ph sensor benzothiazole water soluble fluorescence |
| title | A Highly Water-Soluble Fluorescent and Colorimetric pH Probe |
| title_full | A Highly Water-Soluble Fluorescent and Colorimetric pH Probe |
| title_fullStr | A Highly Water-Soluble Fluorescent and Colorimetric pH Probe |
| title_full_unstemmed | A Highly Water-Soluble Fluorescent and Colorimetric pH Probe |
| title_short | A Highly Water-Soluble Fluorescent and Colorimetric pH Probe |
| title_sort | highly water soluble fluorescent and colorimetric ph probe |
| topic | ph sensor benzothiazole water soluble fluorescence |
| url | https://www.mdpi.com/2073-4352/10/2/83 |
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