Synthesis and luminescent properties of new naphthoquinoline lactone derivatives
Autor(a) principal: | |
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Data de Publicação: | 2020 |
Outros Autores: | , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1016/j.jlumin.2020.117547 http://hdl.handle.net/11449/199153 |
Resumo: | The multicomponent reaction between tetronic acid (1), 2-aminoanthracene (2) and aromatic aldehydes (3) and the subsequent addition of DDQ produced a series of naphtho [2,3-f]quinoline lactone derivatives (5) in good yield. UV–Vis and fluorescence spectra of these derivatives are described. The optical absorption and emission properties of the compounds were studied in different solvents and pH. The results show that the naphthoquinoline derivatives have emission bands of 453–517 nm and one of them, compound 5d, had an unexpected bathochromic shift (597 nm) caused by an excited-state intramolecular proton transfer (ESIPT). The luminescent properties of 5d in different solvents and pH, although preliminary, indicate the potential use of this compound as a chemical sensor. |
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Repositório Institucional da UNESP |
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Synthesis and luminescent properties of new naphthoquinoline lactone derivativesChemical sensorESIPTLuminescent propertiesSolvatochromismStokes shiftThe multicomponent reaction between tetronic acid (1), 2-aminoanthracene (2) and aromatic aldehydes (3) and the subsequent addition of DDQ produced a series of naphtho [2,3-f]quinoline lactone derivatives (5) in good yield. UV–Vis and fluorescence spectra of these derivatives are described. The optical absorption and emission properties of the compounds were studied in different solvents and pH. The results show that the naphthoquinoline derivatives have emission bands of 453–517 nm and one of them, compound 5d, had an unexpected bathochromic shift (597 nm) caused by an excited-state intramolecular proton transfer (ESIPT). The luminescent properties of 5d in different solvents and pH, although preliminary, indicate the potential use of this compound as a chemical sensor.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Departamento de Física e Química Unesp Univ Estadual PaulistaNúcleo de Pesquisas Em Ciências Exatas e Tecnológicas Universidade de FrancaDepartamento de Física e Química Unesp Univ Estadual PaulistaFAPESP: 2018/00544–4Universidade Estadual Paulista (Unesp)Universidade de FrancaSantos, Fernanda Amorim [UNESP]Tondato, Wellington Negri [UNESP]Tame Parreira, Renato LuisOrenha, Renato PereiraLeite Lourenço, Luiz Carlosda Silva de Laurentiz, Rosangela [UNESP]2020-12-12T01:32:07Z2020-12-12T01:32:07Z2020-11-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.1016/j.jlumin.2020.117547Journal of Luminescence, v. 227.0022-2313http://hdl.handle.net/11449/19915310.1016/j.jlumin.2020.1175472-s2.0-85088535730Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengJournal of Luminescenceinfo:eu-repo/semantics/openAccess2021-10-23T04:16:00Zoai:repositorio.unesp.br:11449/199153Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T18:33:46.601695Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Synthesis and luminescent properties of new naphthoquinoline lactone derivatives |
title |
Synthesis and luminescent properties of new naphthoquinoline lactone derivatives |
spellingShingle |
Synthesis and luminescent properties of new naphthoquinoline lactone derivatives Santos, Fernanda Amorim [UNESP] Chemical sensor ESIPT Luminescent properties Solvatochromism Stokes shift |
title_short |
Synthesis and luminescent properties of new naphthoquinoline lactone derivatives |
title_full |
Synthesis and luminescent properties of new naphthoquinoline lactone derivatives |
title_fullStr |
Synthesis and luminescent properties of new naphthoquinoline lactone derivatives |
title_full_unstemmed |
Synthesis and luminescent properties of new naphthoquinoline lactone derivatives |
title_sort |
Synthesis and luminescent properties of new naphthoquinoline lactone derivatives |
author |
Santos, Fernanda Amorim [UNESP] |
author_facet |
Santos, Fernanda Amorim [UNESP] Tondato, Wellington Negri [UNESP] Tame Parreira, Renato Luis Orenha, Renato Pereira Leite Lourenço, Luiz Carlos da Silva de Laurentiz, Rosangela [UNESP] |
author_role |
author |
author2 |
Tondato, Wellington Negri [UNESP] Tame Parreira, Renato Luis Orenha, Renato Pereira Leite Lourenço, Luiz Carlos da Silva de Laurentiz, Rosangela [UNESP] |
author2_role |
author author author author author |
dc.contributor.none.fl_str_mv |
Universidade Estadual Paulista (Unesp) Universidade de Franca |
dc.contributor.author.fl_str_mv |
Santos, Fernanda Amorim [UNESP] Tondato, Wellington Negri [UNESP] Tame Parreira, Renato Luis Orenha, Renato Pereira Leite Lourenço, Luiz Carlos da Silva de Laurentiz, Rosangela [UNESP] |
dc.subject.por.fl_str_mv |
Chemical sensor ESIPT Luminescent properties Solvatochromism Stokes shift |
topic |
Chemical sensor ESIPT Luminescent properties Solvatochromism Stokes shift |
description |
The multicomponent reaction between tetronic acid (1), 2-aminoanthracene (2) and aromatic aldehydes (3) and the subsequent addition of DDQ produced a series of naphtho [2,3-f]quinoline lactone derivatives (5) in good yield. UV–Vis and fluorescence spectra of these derivatives are described. The optical absorption and emission properties of the compounds were studied in different solvents and pH. The results show that the naphthoquinoline derivatives have emission bands of 453–517 nm and one of them, compound 5d, had an unexpected bathochromic shift (597 nm) caused by an excited-state intramolecular proton transfer (ESIPT). The luminescent properties of 5d in different solvents and pH, although preliminary, indicate the potential use of this compound as a chemical sensor. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020-12-12T01:32:07Z 2020-12-12T01:32:07Z 2020-11-01 |
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.jlumin.2020.117547 Journal of Luminescence, v. 227. 0022-2313 http://hdl.handle.net/11449/199153 10.1016/j.jlumin.2020.117547 2-s2.0-85088535730 |
url |
http://dx.doi.org/10.1016/j.jlumin.2020.117547 http://hdl.handle.net/11449/199153 |
identifier_str_mv |
Journal of Luminescence, v. 227. 0022-2313 10.1016/j.jlumin.2020.117547 2-s2.0-85088535730 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Journal of Luminescence |
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_ |
1808128946722570240 |