Synthesis, photophysical characterisation and photostability studies of NIR probes with aliphatic, aromatic and chlorinated terminals in 5- and 9-amino positions of benzo[a]phenoxazines
Autor(a) principal: | |
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Data de Publicação: | 2016 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/1822/44055 |
Resumo: | A new series of benzo[a]phenoxazinium chlorides possessing mono- or disubstituted amines with 3-chloropropyl groups at the 9-position, isopropyl, cyclohexyl and phenyl groups as terminals at 5-postion was synthesised. Photophysical studies were performed in dry ethanol and aqueous solutions. The terminals at the 5-amino position were found to influence the acid-base equilibrium. The presence of hydroxyl functionality at 2-position was found to introduce an additional basic form that is the one in equilibrium with the cationic acid form in dry ethanol solutions. The photostability of these compounds in different media was also investigated and a high resistance to photobleaching in model biological membranes was observed. In proteins a moderate of 20% photobleaching occurs in 1h 30min, while in water more than 60% of the compound molecules are photodegraded during the same time interval. |
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Synthesis, photophysical characterisation and photostability studies of NIR probes with aliphatic, aromatic and chlorinated terminals in 5- and 9-amino positions of benzo[a]phenoxazinesNile BlueBenzo[a]phenoxazinesNear-infrared fluorescent probesPhotostabilityFluorochromophoresCiências Naturais::Ciências FísicasCiências Naturais::Ciências QuímicasScience & TechnologyA new series of benzo[a]phenoxazinium chlorides possessing mono- or disubstituted amines with 3-chloropropyl groups at the 9-position, isopropyl, cyclohexyl and phenyl groups as terminals at 5-postion was synthesised. Photophysical studies were performed in dry ethanol and aqueous solutions. The terminals at the 5-amino position were found to influence the acid-base equilibrium. The presence of hydroxyl functionality at 2-position was found to introduce an additional basic form that is the one in equilibrium with the cationic acid form in dry ethanol solutions. The photostability of these compounds in different media was also investigated and a high resistance to photobleaching in model biological membranes was observed. In proteins a moderate of 20% photobleaching occurs in 1h 30min, while in water more than 60% of the compound molecules are photodegraded during the same time interval.Thanks are due to the Fundação para a Ciência e Tecnologia (FCT, Portugal) for financial support to the NMR portuguese network (PTNMR, Bruker Avance III 400-Univ. Minho), FCT and FEDER (European Fund for Regional Development)-COMPETE-QREN-EU for financial support to Research Centres CQ/UM [PEst-C/QUI/UI0686/2013 (FCOMP-01-0124-FEDER-037302)] and CFUM [PEst-C/FIS/UI0607/2013 (F-COMP-01-0124-FEDER-022711)]. Post-doctoral grant to B. R. Raju (SFRH/BPD/62881/2009) is also acknowledged to FCT, POPH-QREN, FSE.ElsevierUniversidade do MinhoRaju, B. RamaCarvalho, Marcello M.T.Leitão, Maria Inês P.S.Coutinho, Paulo J. G.Gonçalves, M. Sameiro T.20162016-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/44055eng94. Raju, B. R., Carvalho, M. M. T., Leitão, M. I. P. S., Coutinho, P. J. G., & Gonçalves, M. S. T. (2016). Synthesis, photophysical characterisation and photostability studies of NIR probes with aliphatic, aromatic and chlorinated terminals in 5- and 9-amino positions of benzo[a]phenoxazines. Dyes and Pigments, 132, 204-212. doi: 10.1016/j.dyepig.2016.04.0490143-720810.1016/j.dyepig.2016.04.049http://www.sciencedirect.com/science/article/pii/S0143720816301784info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T12:31:55Zoai:repositorium.sdum.uminho.pt:1822/44055Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:27:14.089574Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Synthesis, photophysical characterisation and photostability studies of NIR probes with aliphatic, aromatic and chlorinated terminals in 5- and 9-amino positions of benzo[a]phenoxazines |
title |
Synthesis, photophysical characterisation and photostability studies of NIR probes with aliphatic, aromatic and chlorinated terminals in 5- and 9-amino positions of benzo[a]phenoxazines |
spellingShingle |
Synthesis, photophysical characterisation and photostability studies of NIR probes with aliphatic, aromatic and chlorinated terminals in 5- and 9-amino positions of benzo[a]phenoxazines Raju, B. Rama Nile Blue Benzo[a]phenoxazines Near-infrared fluorescent probes Photostability Fluorochromophores Ciências Naturais::Ciências Físicas Ciências Naturais::Ciências Químicas Science & Technology |
title_short |
Synthesis, photophysical characterisation and photostability studies of NIR probes with aliphatic, aromatic and chlorinated terminals in 5- and 9-amino positions of benzo[a]phenoxazines |
title_full |
Synthesis, photophysical characterisation and photostability studies of NIR probes with aliphatic, aromatic and chlorinated terminals in 5- and 9-amino positions of benzo[a]phenoxazines |
title_fullStr |
Synthesis, photophysical characterisation and photostability studies of NIR probes with aliphatic, aromatic and chlorinated terminals in 5- and 9-amino positions of benzo[a]phenoxazines |
title_full_unstemmed |
Synthesis, photophysical characterisation and photostability studies of NIR probes with aliphatic, aromatic and chlorinated terminals in 5- and 9-amino positions of benzo[a]phenoxazines |
title_sort |
Synthesis, photophysical characterisation and photostability studies of NIR probes with aliphatic, aromatic and chlorinated terminals in 5- and 9-amino positions of benzo[a]phenoxazines |
author |
Raju, B. Rama |
author_facet |
Raju, B. Rama Carvalho, Marcello M.T. Leitão, Maria Inês P.S. Coutinho, Paulo J. G. Gonçalves, M. Sameiro T. |
author_role |
author |
author2 |
Carvalho, Marcello M.T. Leitão, Maria Inês P.S. Coutinho, Paulo J. G. Gonçalves, M. Sameiro T. |
author2_role |
author author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Raju, B. Rama Carvalho, Marcello M.T. Leitão, Maria Inês P.S. Coutinho, Paulo J. G. Gonçalves, M. Sameiro T. |
dc.subject.por.fl_str_mv |
Nile Blue Benzo[a]phenoxazines Near-infrared fluorescent probes Photostability Fluorochromophores Ciências Naturais::Ciências Físicas Ciências Naturais::Ciências Químicas Science & Technology |
topic |
Nile Blue Benzo[a]phenoxazines Near-infrared fluorescent probes Photostability Fluorochromophores Ciências Naturais::Ciências Físicas Ciências Naturais::Ciências Químicas Science & Technology |
description |
A new series of benzo[a]phenoxazinium chlorides possessing mono- or disubstituted amines with 3-chloropropyl groups at the 9-position, isopropyl, cyclohexyl and phenyl groups as terminals at 5-postion was synthesised. Photophysical studies were performed in dry ethanol and aqueous solutions. The terminals at the 5-amino position were found to influence the acid-base equilibrium. The presence of hydroxyl functionality at 2-position was found to introduce an additional basic form that is the one in equilibrium with the cationic acid form in dry ethanol solutions. The photostability of these compounds in different media was also investigated and a high resistance to photobleaching in model biological membranes was observed. In proteins a moderate of 20% photobleaching occurs in 1h 30min, while in water more than 60% of the compound molecules are photodegraded during the same time interval. |
publishDate |
2016 |
dc.date.none.fl_str_mv |
2016 2016-01-01T00:00:00Z |
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://hdl.handle.net/1822/44055 |
url |
http://hdl.handle.net/1822/44055 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
94. Raju, B. R., Carvalho, M. M. T., Leitão, M. I. P. S., Coutinho, P. J. G., & Gonçalves, M. S. T. (2016). Synthesis, photophysical characterisation and photostability studies of NIR probes with aliphatic, aromatic and chlorinated terminals in 5- and 9-amino positions of benzo[a]phenoxazines. Dyes and Pigments, 132, 204-212. doi: 10.1016/j.dyepig.2016.04.049 0143-7208 10.1016/j.dyepig.2016.04.049 http://www.sciencedirect.com/science/article/pii/S0143720816301784 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Elsevier |
publisher.none.fl_str_mv |
Elsevier |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
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RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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