N-(Di)icosyl-substituted benzo[a]phenoxazinium chlorides : synthesis and evaluation as near-infrared membrane probes
Autor(a) principal: | |
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Data de Publicação: | 2011 |
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/1822/13091 |
Resumo: | Five benzo[a]phenoxazinium chlorides containing alkyl chains with twenty carbon atoms on 5- or 9-positions of the tetracyclic ring were efficiently synthesised and characterised by UV/Vis/NIR spectroscopy. The absorption and emission maxima in ethanol lie in the range 627-641 nm and 645-676 nm, respectively, with quantum yields varying from 0.14 to 0.38. Preliminary photophysical studies with these fluorochromophores in zwitterionic (2,3- bis(palmitoyl-oxy)propyl-2-(trimethylammonio)ethyl phosphate, DPPC) and cationic (N,N-dimethyl-N-octadecyloctadecan-1-aminium bromide, DODAB) vesicles were carried out. The results showed that the new benzo[a]phenoxazinium derivatives are able to detect the gel to liquid-crystalline lipid phase transition through variations, either in the H-aggregation extent or in an acid-base equilibrium. |
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N-(Di)icosyl-substituted benzo[a]phenoxazinium chlorides : synthesis and evaluation as near-infrared membrane probesBenzo[a]phenoxazinium dyesMembrane probesNear-infrared labelsNile blueCationic dyesFluorescent probesMembranesVesiclesSurfactantsImaging agentsScience & TechnologyFive benzo[a]phenoxazinium chlorides containing alkyl chains with twenty carbon atoms on 5- or 9-positions of the tetracyclic ring were efficiently synthesised and characterised by UV/Vis/NIR spectroscopy. The absorption and emission maxima in ethanol lie in the range 627-641 nm and 645-676 nm, respectively, with quantum yields varying from 0.14 to 0.38. Preliminary photophysical studies with these fluorochromophores in zwitterionic (2,3- bis(palmitoyl-oxy)propyl-2-(trimethylammonio)ethyl phosphate, DPPC) and cationic (N,N-dimethyl-N-octadecyloctadecan-1-aminium bromide, DODAB) vesicles were carried out. The results showed that the new benzo[a]phenoxazinium derivatives are able to detect the gel to liquid-crystalline lipid phase transition through variations, either in the H-aggregation extent or in an acid-base equilibrium.Fundação para a Ciência e Tecnologia (FCT) - REDE/1517/RMN/2005Fundo Europeu de Desenvolvimento Regional (FEDER) - POCI 2010Wiley-BlackwellUniversidade do MinhoNaik, SaralaAlves, Carla M. A.Coutinho, Paulo J. G.Gonçalves, M. Sameiro T.2011-052011-05-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/13091eng1434-193X10.1002/ejoc.201001579http://onlinelibrary.wiley.com/info: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:RCAAP2023-07-21T11:58:27Zoai:repositorium.sdum.uminho.pt:1822/13091Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T18:48:10.198550Repositório 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 |
N-(Di)icosyl-substituted benzo[a]phenoxazinium chlorides : synthesis and evaluation as near-infrared membrane probes |
title |
N-(Di)icosyl-substituted benzo[a]phenoxazinium chlorides : synthesis and evaluation as near-infrared membrane probes |
spellingShingle |
N-(Di)icosyl-substituted benzo[a]phenoxazinium chlorides : synthesis and evaluation as near-infrared membrane probes Naik, Sarala Benzo[a]phenoxazinium dyes Membrane probes Near-infrared labels Nile blue Cationic dyes Fluorescent probes Membranes Vesicles Surfactants Imaging agents Science & Technology |
title_short |
N-(Di)icosyl-substituted benzo[a]phenoxazinium chlorides : synthesis and evaluation as near-infrared membrane probes |
title_full |
N-(Di)icosyl-substituted benzo[a]phenoxazinium chlorides : synthesis and evaluation as near-infrared membrane probes |
title_fullStr |
N-(Di)icosyl-substituted benzo[a]phenoxazinium chlorides : synthesis and evaluation as near-infrared membrane probes |
title_full_unstemmed |
N-(Di)icosyl-substituted benzo[a]phenoxazinium chlorides : synthesis and evaluation as near-infrared membrane probes |
title_sort |
N-(Di)icosyl-substituted benzo[a]phenoxazinium chlorides : synthesis and evaluation as near-infrared membrane probes |
author |
Naik, Sarala |
author_facet |
Naik, Sarala Alves, Carla M. A. Coutinho, Paulo J. G. Gonçalves, M. Sameiro T. |
author_role |
author |
author2 |
Alves, Carla M. A. Coutinho, Paulo J. G. Gonçalves, M. Sameiro T. |
author2_role |
author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Naik, Sarala Alves, Carla M. A. Coutinho, Paulo J. G. Gonçalves, M. Sameiro T. |
dc.subject.por.fl_str_mv |
Benzo[a]phenoxazinium dyes Membrane probes Near-infrared labels Nile blue Cationic dyes Fluorescent probes Membranes Vesicles Surfactants Imaging agents Science & Technology |
topic |
Benzo[a]phenoxazinium dyes Membrane probes Near-infrared labels Nile blue Cationic dyes Fluorescent probes Membranes Vesicles Surfactants Imaging agents Science & Technology |
description |
Five benzo[a]phenoxazinium chlorides containing alkyl chains with twenty carbon atoms on 5- or 9-positions of the tetracyclic ring were efficiently synthesised and characterised by UV/Vis/NIR spectroscopy. The absorption and emission maxima in ethanol lie in the range 627-641 nm and 645-676 nm, respectively, with quantum yields varying from 0.14 to 0.38. Preliminary photophysical studies with these fluorochromophores in zwitterionic (2,3- bis(palmitoyl-oxy)propyl-2-(trimethylammonio)ethyl phosphate, DPPC) and cationic (N,N-dimethyl-N-octadecyloctadecan-1-aminium bromide, DODAB) vesicles were carried out. The results showed that the new benzo[a]phenoxazinium derivatives are able to detect the gel to liquid-crystalline lipid phase transition through variations, either in the H-aggregation extent or in an acid-base equilibrium. |
publishDate |
2011 |
dc.date.none.fl_str_mv |
2011-05 2011-05-01T00:00:00Z |
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/1822/13091 |
url |
http://hdl.handle.net/1822/13091 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
1434-193X 10.1002/ejoc.201001579 http://onlinelibrary.wiley.com/ |
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 |
Wiley-Blackwell |
publisher.none.fl_str_mv |
Wiley-Blackwell |
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 |
instname_str |
Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository.name.fl_str_mv |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
repository.mail.fl_str_mv |
|
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1799132241984487424 |