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

Detalhes bibliográficos
Autor(a) principal: Raju, B. Rama
Data de Publicação: 2016
Outros Autores: Carvalho, Marcello M.T., Leitão, Maria Inês P.S., Coutinho, Paulo J. G., Gonçalves, M. Sameiro T.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
Texto Completo: https://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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spelling 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/pdfhttps://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:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)instname:FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiainstacron:RCAAP2025-04-12T04:57:18Zoai:repositorium.sdum.uminho.pt:1822/44055Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireinfo@rcaap.ptopendoar:https://opendoar.ac.uk/repository/71602025-05-28T15:49:12.449928Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) - FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiafalse
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 https://hdl.handle.net/1822/44055
url https://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:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
instname:FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
instacron:RCAAP
instname_str FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
instacron_str RCAAP
institution RCAAP
reponame_str Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
collection Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
repository.name.fl_str_mv Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) - FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
repository.mail.fl_str_mv info@rcaap.pt
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