N-(Di)icosyl-substituted benzo[a]phenoxazinium chlorides : synthesis and evaluation as near-infrared membrane probes

Detalhes bibliográficos
Autor(a) principal: Naik, Sarala
Data de Publicação: 2011
Outros Autores: Alves, Carla M. A., 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: 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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spelling 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:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)instname:FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiainstacron:RCAAP2024-05-11T04:25:50Zoai:repositorium.sdum.uminho.pt:1822/13091Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireinfo@rcaap.ptopendoar:https://opendoar.ac.uk/repository/71602025-05-28T14:48:11.028339Repositórios 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 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: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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