Water-Soluble Benzazole Dyes Fluorescent by ESIPT: Structural Characterization, Photophysical Properties and Its Application as a Probe for Direct Staining of Helminths
Autor(a) principal: | |
---|---|
Data de Publicação: | 2019 |
Outros Autores: | , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000300509 |
Resumo: | A series of four water-soluble benzazole dyes that emit fluorescence by the excited state intramolecular proton transfer (ESIPT) mechanism were structurally characterized by Fourier transform infrared spectroscopy (FTIR), 1H and 13C nuclear magnetic resonance (NMR) attached proton test (APT) and mass spectrometry. Their photophysical properties were systematically studied by UV-absorption and fluorescence emission. Some photophysical parameters were obtained by semi-empirical PM3 and ZINDO methods, and related to experimental photophysical data. Changes in the absorption and fluorescence emission spectra as well as conformational equilibrium between different species were investigated in solvents of different polarities and under different pH conditions. These benzazole dyes emit dual fluorescence emission in the blue-orange region with a Stokes shift between 2617-12337 cm-1. In general, these dyes are potentially interesting for studies of biological systems in an aqueous environment due to the presence of groups that increase aqueous solubility and reactivity with biomolecules. The present dyes were successfully used as new probes by means of direct staining of larvae. The obtained results indicate that these fluorescent dyes permit a quick, easy and selective visualization of larvae. |
id |
SBQ-2_85be4b9a0a01288ac2f4f026277fb16c |
---|---|
oai_identifier_str |
oai:scielo:S0103-50532019000300509 |
network_acronym_str |
SBQ-2 |
network_name_str |
Journal of the Brazilian Chemical Society (Online) |
repository_id_str |
|
spelling |
Water-Soluble Benzazole Dyes Fluorescent by ESIPT: Structural Characterization, Photophysical Properties and Its Application as a Probe for Direct Staining of Helminthsheterocyclic compoundsproton transferconformational equilibriumfluorescencehelminthsA series of four water-soluble benzazole dyes that emit fluorescence by the excited state intramolecular proton transfer (ESIPT) mechanism were structurally characterized by Fourier transform infrared spectroscopy (FTIR), 1H and 13C nuclear magnetic resonance (NMR) attached proton test (APT) and mass spectrometry. Their photophysical properties were systematically studied by UV-absorption and fluorescence emission. Some photophysical parameters were obtained by semi-empirical PM3 and ZINDO methods, and related to experimental photophysical data. Changes in the absorption and fluorescence emission spectra as well as conformational equilibrium between different species were investigated in solvents of different polarities and under different pH conditions. These benzazole dyes emit dual fluorescence emission in the blue-orange region with a Stokes shift between 2617-12337 cm-1. In general, these dyes are potentially interesting for studies of biological systems in an aqueous environment due to the presence of groups that increase aqueous solubility and reactivity with biomolecules. The present dyes were successfully used as new probes by means of direct staining of larvae. The obtained results indicate that these fluorescent dyes permit a quick, easy and selective visualization of larvae.Sociedade Brasileira de Química2019-03-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000300509Journal of the Brazilian Chemical Society v.30 n.3 2019reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20180193info:eu-repo/semantics/openAccessBarros,Hélio L.Marques,Sandra M. T.Stefani,Valtereng2019-02-14T00:00:00Zoai:scielo:S0103-50532019000300509Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2019-02-14T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Water-Soluble Benzazole Dyes Fluorescent by ESIPT: Structural Characterization, Photophysical Properties and Its Application as a Probe for Direct Staining of Helminths |
title |
Water-Soluble Benzazole Dyes Fluorescent by ESIPT: Structural Characterization, Photophysical Properties and Its Application as a Probe for Direct Staining of Helminths |
spellingShingle |
Water-Soluble Benzazole Dyes Fluorescent by ESIPT: Structural Characterization, Photophysical Properties and Its Application as a Probe for Direct Staining of Helminths Barros,Hélio L. heterocyclic compounds proton transfer conformational equilibrium fluorescence helminths |
title_short |
Water-Soluble Benzazole Dyes Fluorescent by ESIPT: Structural Characterization, Photophysical Properties and Its Application as a Probe for Direct Staining of Helminths |
title_full |
Water-Soluble Benzazole Dyes Fluorescent by ESIPT: Structural Characterization, Photophysical Properties and Its Application as a Probe for Direct Staining of Helminths |
title_fullStr |
Water-Soluble Benzazole Dyes Fluorescent by ESIPT: Structural Characterization, Photophysical Properties and Its Application as a Probe for Direct Staining of Helminths |
title_full_unstemmed |
Water-Soluble Benzazole Dyes Fluorescent by ESIPT: Structural Characterization, Photophysical Properties and Its Application as a Probe for Direct Staining of Helminths |
title_sort |
Water-Soluble Benzazole Dyes Fluorescent by ESIPT: Structural Characterization, Photophysical Properties and Its Application as a Probe for Direct Staining of Helminths |
author |
Barros,Hélio L. |
author_facet |
Barros,Hélio L. Marques,Sandra M. T. Stefani,Valter |
author_role |
author |
author2 |
Marques,Sandra M. T. Stefani,Valter |
author2_role |
author author |
dc.contributor.author.fl_str_mv |
Barros,Hélio L. Marques,Sandra M. T. Stefani,Valter |
dc.subject.por.fl_str_mv |
heterocyclic compounds proton transfer conformational equilibrium fluorescence helminths |
topic |
heterocyclic compounds proton transfer conformational equilibrium fluorescence helminths |
description |
A series of four water-soluble benzazole dyes that emit fluorescence by the excited state intramolecular proton transfer (ESIPT) mechanism were structurally characterized by Fourier transform infrared spectroscopy (FTIR), 1H and 13C nuclear magnetic resonance (NMR) attached proton test (APT) and mass spectrometry. Their photophysical properties were systematically studied by UV-absorption and fluorescence emission. Some photophysical parameters were obtained by semi-empirical PM3 and ZINDO methods, and related to experimental photophysical data. Changes in the absorption and fluorescence emission spectra as well as conformational equilibrium between different species were investigated in solvents of different polarities and under different pH conditions. These benzazole dyes emit dual fluorescence emission in the blue-orange region with a Stokes shift between 2617-12337 cm-1. In general, these dyes are potentially interesting for studies of biological systems in an aqueous environment due to the presence of groups that increase aqueous solubility and reactivity with biomolecules. The present dyes were successfully used as new probes by means of direct staining of larvae. The obtained results indicate that these fluorescent dyes permit a quick, easy and selective visualization of larvae. |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-03-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000300509 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000300509 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0103-5053.20180193 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.30 n.3 2019 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
_version_ |
1750318181647384576 |