Small Schiff base molecules derived from salicylaldehyde as colorimetric and fluorescent neutral-to-basic pH sensors
Autor(a) principal: | |
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Data de Publicação: | 2023 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1016/j.dyepig.2023.111191 http://hdl.handle.net/11449/246939 |
Resumo: | The development of pH sensors is very important to distinguish different pHs in several applications. In this study, we examined the change of the side chain moiety on the photophysical properties of eight pH-sensitive small Schiff bases (SBs) that can act as both, colorimetric and fluorometric probes. For that, we synthesized all SBs by condensation between salicylaldehyde with a primary amine (methyl-, ethyl-, isopropyl, propyl-, butyl-, pentyl-, cyclohexyl-, and benzyl-amine). The complete molecular structure was confirmed by 1H NMR, 13C NMR, FTIR, UV–Vis, and by GC–FID purity over 90% was confirmed for all synthesized SBs. Theoretical calculations were also performed to give support to our findings. All synthesized samples were tested as a colorimetric and fluorometric pH sensor in the range of pH 3.0–12.0. All SBs exhibited similar behavior, despite the side chain lengths. The SBs are quite long-lived in water solution, allowing their usage as pH sensor. While between pH 3.0–7.0 they are colorless due to the presence of the protonated species, HSB, above pH 7.0 they turn yellow due to the formation of SB−, indicating that the chromogenic property depends on the pH. Additionally, these SBs also exhibit fluorogenic characteristic as they show fluorescence off at acidic pH 3.0–7.0 and fluorescence on (508 nm) above pH 8.0, exhibiting a linear response between pH 7.0–9.0. The pKa value was calculated using the Henderson–Hasselbalch equation for all SBs, obtaining values from 8.20 to 8.52. All SBs act as pH-sensitive colorimetric and fluorometric probes in neutral-to-basic solutions and this process is reversible. |
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Small Schiff base molecules derived from salicylaldehyde as colorimetric and fluorescent neutral-to-basic pH sensorsChromogenic sensorFluorogenic sensorpKa Schiff baseProbeThe development of pH sensors is very important to distinguish different pHs in several applications. In this study, we examined the change of the side chain moiety on the photophysical properties of eight pH-sensitive small Schiff bases (SBs) that can act as both, colorimetric and fluorometric probes. For that, we synthesized all SBs by condensation between salicylaldehyde with a primary amine (methyl-, ethyl-, isopropyl, propyl-, butyl-, pentyl-, cyclohexyl-, and benzyl-amine). The complete molecular structure was confirmed by 1H NMR, 13C NMR, FTIR, UV–Vis, and by GC–FID purity over 90% was confirmed for all synthesized SBs. Theoretical calculations were also performed to give support to our findings. All synthesized samples were tested as a colorimetric and fluorometric pH sensor in the range of pH 3.0–12.0. All SBs exhibited similar behavior, despite the side chain lengths. The SBs are quite long-lived in water solution, allowing their usage as pH sensor. While between pH 3.0–7.0 they are colorless due to the presence of the protonated species, HSB, above pH 7.0 they turn yellow due to the formation of SB−, indicating that the chromogenic property depends on the pH. Additionally, these SBs also exhibit fluorogenic characteristic as they show fluorescence off at acidic pH 3.0–7.0 and fluorescence on (508 nm) above pH 8.0, exhibiting a linear response between pH 7.0–9.0. The pKa value was calculated using the Henderson–Hasselbalch equation for all SBs, obtaining values from 8.20 to 8.52. All SBs act as pH-sensitive colorimetric and fluorometric probes in neutral-to-basic solutions and this process is reversible.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)São Paulo State University (Unesp) Institute of Biosciences Humanities and Exact Sciences, São José Do Rio Preto, SPSão Paulo State University (Unesp) School of Technology and Sciences, SPSão Paulo State University (Unesp) Institute of Chemistry, SPSão Paulo State University (Unesp) Institute of Biosciences Humanities and Exact Sciences, São José Do Rio Preto, SPSão Paulo State University (Unesp) School of Technology and Sciences, SPSão Paulo State University (Unesp) Institute of Chemistry, SPFAPESP: 2017/24062–6FAPESP: 2019/26103–7CNPq: 304003/2018–1CNPq: 308868/2022-6CAPES: 88887.484955/2020–00CAPES: 88887.686158/2022–00Universidade Estadual Paulista (UNESP)Silva, Renan C. [UNESP]Canisares, Felipe S.M. [UNESP]Mutti, Alessandra M.G. [UNESP]Pires, Ana M. [UNESP]Lima, Sergio A.M. [UNESP]2023-07-29T12:54:44Z2023-07-29T12:54:44Z2023-05-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.1016/j.dyepig.2023.111191Dyes and Pigments, v. 213.1873-37430143-7208http://hdl.handle.net/11449/24693910.1016/j.dyepig.2023.1111912-s2.0-85149390730Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengDyes and Pigmentsinfo:eu-repo/semantics/openAccess2023-07-29T12:54:44Zoai:repositorio.unesp.br:11449/246939Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462023-07-29T12:54:44Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Small Schiff base molecules derived from salicylaldehyde as colorimetric and fluorescent neutral-to-basic pH sensors |
title |
Small Schiff base molecules derived from salicylaldehyde as colorimetric and fluorescent neutral-to-basic pH sensors |
spellingShingle |
Small Schiff base molecules derived from salicylaldehyde as colorimetric and fluorescent neutral-to-basic pH sensors Silva, Renan C. [UNESP] Chromogenic sensor Fluorogenic sensor pKa Schiff base Probe |
title_short |
Small Schiff base molecules derived from salicylaldehyde as colorimetric and fluorescent neutral-to-basic pH sensors |
title_full |
Small Schiff base molecules derived from salicylaldehyde as colorimetric and fluorescent neutral-to-basic pH sensors |
title_fullStr |
Small Schiff base molecules derived from salicylaldehyde as colorimetric and fluorescent neutral-to-basic pH sensors |
title_full_unstemmed |
Small Schiff base molecules derived from salicylaldehyde as colorimetric and fluorescent neutral-to-basic pH sensors |
title_sort |
Small Schiff base molecules derived from salicylaldehyde as colorimetric and fluorescent neutral-to-basic pH sensors |
author |
Silva, Renan C. [UNESP] |
author_facet |
Silva, Renan C. [UNESP] Canisares, Felipe S.M. [UNESP] Mutti, Alessandra M.G. [UNESP] Pires, Ana M. [UNESP] Lima, Sergio A.M. [UNESP] |
author_role |
author |
author2 |
Canisares, Felipe S.M. [UNESP] Mutti, Alessandra M.G. [UNESP] Pires, Ana M. [UNESP] Lima, Sergio A.M. [UNESP] |
author2_role |
author author author author |
dc.contributor.none.fl_str_mv |
Universidade Estadual Paulista (UNESP) |
dc.contributor.author.fl_str_mv |
Silva, Renan C. [UNESP] Canisares, Felipe S.M. [UNESP] Mutti, Alessandra M.G. [UNESP] Pires, Ana M. [UNESP] Lima, Sergio A.M. [UNESP] |
dc.subject.por.fl_str_mv |
Chromogenic sensor Fluorogenic sensor pKa Schiff base Probe |
topic |
Chromogenic sensor Fluorogenic sensor pKa Schiff base Probe |
description |
The development of pH sensors is very important to distinguish different pHs in several applications. In this study, we examined the change of the side chain moiety on the photophysical properties of eight pH-sensitive small Schiff bases (SBs) that can act as both, colorimetric and fluorometric probes. For that, we synthesized all SBs by condensation between salicylaldehyde with a primary amine (methyl-, ethyl-, isopropyl, propyl-, butyl-, pentyl-, cyclohexyl-, and benzyl-amine). The complete molecular structure was confirmed by 1H NMR, 13C NMR, FTIR, UV–Vis, and by GC–FID purity over 90% was confirmed for all synthesized SBs. Theoretical calculations were also performed to give support to our findings. All synthesized samples were tested as a colorimetric and fluorometric pH sensor in the range of pH 3.0–12.0. All SBs exhibited similar behavior, despite the side chain lengths. The SBs are quite long-lived in water solution, allowing their usage as pH sensor. While between pH 3.0–7.0 they are colorless due to the presence of the protonated species, HSB, above pH 7.0 they turn yellow due to the formation of SB−, indicating that the chromogenic property depends on the pH. Additionally, these SBs also exhibit fluorogenic characteristic as they show fluorescence off at acidic pH 3.0–7.0 and fluorescence on (508 nm) above pH 8.0, exhibiting a linear response between pH 7.0–9.0. The pKa value was calculated using the Henderson–Hasselbalch equation for all SBs, obtaining values from 8.20 to 8.52. All SBs act as pH-sensitive colorimetric and fluorometric probes in neutral-to-basic solutions and this process is reversible. |
publishDate |
2023 |
dc.date.none.fl_str_mv |
2023-07-29T12:54:44Z 2023-07-29T12:54:44Z 2023-05-01 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.1016/j.dyepig.2023.111191 Dyes and Pigments, v. 213. 1873-3743 0143-7208 http://hdl.handle.net/11449/246939 10.1016/j.dyepig.2023.111191 2-s2.0-85149390730 |
url |
http://dx.doi.org/10.1016/j.dyepig.2023.111191 http://hdl.handle.net/11449/246939 |
identifier_str_mv |
Dyes and Pigments, v. 213. 1873-3743 0143-7208 10.1016/j.dyepig.2023.111191 2-s2.0-85149390730 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Dyes and Pigments |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.source.none.fl_str_mv |
Scopus reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
|
_version_ |
1792961471092621312 |