4-(Pyren-1-ylimino)methylphenol and its Silylated Derivative as Chromogenic Chemosensors Highly Selective for Fluoride or Cyanide
Autor(a) principal: | |
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Data de Publicação: | 2015 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532015001202507 |
Resumo: | Two novel compounds, 4-(pyren-1-ylimino)methylphenol and 4-[(triisopropylsilyl)oxy]phenylmethylenepyren-1-amine) were synthesized. Solutions of 4-(pyren-1-ylimino)methylphenol in dimethyl sulfoxide (DMSO) are colorless, but on addition of cyanide and fluoride they become colored due to the deprotonation of the chemosensor. The system is highly selective toward cyanide with the addition of water. This compound can be solubilized in water with addition of cetyltrimethylammonium bromide above its critical micellar concentration. The pKa of the compound in water was determined as 10.49 ± 0.02 and this value is lowered in micellar medium to 7.49 ± 0.02, which means that only cyanide is sufficiently basic to achieve the deprotonation of the compound. Solutions of 4-[(triisopropylsilyl)oxy]phenylmethylenepyren-1-amine) in DMSO are colorless, but they are colored in the presence of cyanide and fluoride and only cyanide could be detected in DMSO-water mixture. The nucleophilic attack of the anions on the silicon center of the compound releases colored 4-(pyren-1-ylimino)methylphenolate, enabling the detection of nucleophilic analytes. |
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4-(Pyren-1-ylimino)methylphenol and its Silylated Derivative as Chromogenic Chemosensors Highly Selective for Fluoride or Cyanidechemodosimeterchromogenic chemosensornaked-eye detectionanion sensingcyanideTwo novel compounds, 4-(pyren-1-ylimino)methylphenol and 4-[(triisopropylsilyl)oxy]phenylmethylenepyren-1-amine) were synthesized. Solutions of 4-(pyren-1-ylimino)methylphenol in dimethyl sulfoxide (DMSO) are colorless, but on addition of cyanide and fluoride they become colored due to the deprotonation of the chemosensor. The system is highly selective toward cyanide with the addition of water. This compound can be solubilized in water with addition of cetyltrimethylammonium bromide above its critical micellar concentration. The pKa of the compound in water was determined as 10.49 ± 0.02 and this value is lowered in micellar medium to 7.49 ± 0.02, which means that only cyanide is sufficiently basic to achieve the deprotonation of the compound. Solutions of 4-[(triisopropylsilyl)oxy]phenylmethylenepyren-1-amine) in DMSO are colorless, but they are colored in the presence of cyanide and fluoride and only cyanide could be detected in DMSO-water mixture. The nucleophilic attack of the anions on the silicon center of the compound releases colored 4-(pyren-1-ylimino)methylphenolate, enabling the detection of nucleophilic analytes.Sociedade Brasileira de Química2015-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532015001202507Journal of the Brazilian Chemical Society v.26 n.12 2015reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20150149info:eu-repo/semantics/openAccessBuske,Jonatan L. O.Nicoleti,Celso R.Cavallaro,Aluisio A.Machado,Vanderlei G.eng2015-12-16T00:00:00Zoai:scielo:S0103-50532015001202507Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2015-12-16T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
4-(Pyren-1-ylimino)methylphenol and its Silylated Derivative as Chromogenic Chemosensors Highly Selective for Fluoride or Cyanide |
title |
4-(Pyren-1-ylimino)methylphenol and its Silylated Derivative as Chromogenic Chemosensors Highly Selective for Fluoride or Cyanide |
spellingShingle |
4-(Pyren-1-ylimino)methylphenol and its Silylated Derivative as Chromogenic Chemosensors Highly Selective for Fluoride or Cyanide Buske,Jonatan L. O. chemodosimeter chromogenic chemosensor naked-eye detection anion sensing cyanide |
title_short |
4-(Pyren-1-ylimino)methylphenol and its Silylated Derivative as Chromogenic Chemosensors Highly Selective for Fluoride or Cyanide |
title_full |
4-(Pyren-1-ylimino)methylphenol and its Silylated Derivative as Chromogenic Chemosensors Highly Selective for Fluoride or Cyanide |
title_fullStr |
4-(Pyren-1-ylimino)methylphenol and its Silylated Derivative as Chromogenic Chemosensors Highly Selective for Fluoride or Cyanide |
title_full_unstemmed |
4-(Pyren-1-ylimino)methylphenol and its Silylated Derivative as Chromogenic Chemosensors Highly Selective for Fluoride or Cyanide |
title_sort |
4-(Pyren-1-ylimino)methylphenol and its Silylated Derivative as Chromogenic Chemosensors Highly Selective for Fluoride or Cyanide |
author |
Buske,Jonatan L. O. |
author_facet |
Buske,Jonatan L. O. Nicoleti,Celso R. Cavallaro,Aluisio A. Machado,Vanderlei G. |
author_role |
author |
author2 |
Nicoleti,Celso R. Cavallaro,Aluisio A. Machado,Vanderlei G. |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
Buske,Jonatan L. O. Nicoleti,Celso R. Cavallaro,Aluisio A. Machado,Vanderlei G. |
dc.subject.por.fl_str_mv |
chemodosimeter chromogenic chemosensor naked-eye detection anion sensing cyanide |
topic |
chemodosimeter chromogenic chemosensor naked-eye detection anion sensing cyanide |
description |
Two novel compounds, 4-(pyren-1-ylimino)methylphenol and 4-[(triisopropylsilyl)oxy]phenylmethylenepyren-1-amine) were synthesized. Solutions of 4-(pyren-1-ylimino)methylphenol in dimethyl sulfoxide (DMSO) are colorless, but on addition of cyanide and fluoride they become colored due to the deprotonation of the chemosensor. The system is highly selective toward cyanide with the addition of water. This compound can be solubilized in water with addition of cetyltrimethylammonium bromide above its critical micellar concentration. The pKa of the compound in water was determined as 10.49 ± 0.02 and this value is lowered in micellar medium to 7.49 ± 0.02, which means that only cyanide is sufficiently basic to achieve the deprotonation of the compound. Solutions of 4-[(triisopropylsilyl)oxy]phenylmethylenepyren-1-amine) in DMSO are colorless, but they are colored in the presence of cyanide and fluoride and only cyanide could be detected in DMSO-water mixture. The nucleophilic attack of the anions on the silicon center of the compound releases colored 4-(pyren-1-ylimino)methylphenolate, enabling the detection of nucleophilic analytes. |
publishDate |
2015 |
dc.date.none.fl_str_mv |
2015-12-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532015001202507 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532015001202507 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.5935/0103-5053.20150149 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.26 n.12 2015 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
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1750318177864122368 |