Please use this identifier to cite or link to this item: http://hdl.handle.net/1822/11743

TitleSynthesis and photophysical studies of new fluorescent indole derivatives obtained from β-Bromodehydroamino acids : interaction with fluoride anions
Author(s)Pereira, Goreti
Castanheira, Elisabete M. S.
Ferreira, Paula M. T.
Queiroz, Maria João R. P.
KeywordsSuzuki–Miyaura coupling
Metal-assisted cyclization
Indoles
Fluorescent probes
Fluorides
Nitrogen heterocycles
Cyclization
Issue dateJan-2010
PublisherWiley
JournalEuropean Journal of Organic Chemistry
Citation"European Journal of Organic Chemistry". ISSN 1434-193X. (2010) 464-475.
Abstract(s)Several new indole derivatives were synthesised from β-brominated dehydroamino acids and arylboronic acids by using a strategy developed in our research group that involves a sequential Suzuki–Miyaura cross-coupling reaction and a metal-assisted C–N intramolecular cyclisation. The cyclised products were obtained either by direct cyclisation or by isomerisation followed by cyclisation. The photophysical properties of these compounds were studied in four solvents of different polarity (cyclohexane, diethyl ether, acetonitrile and ethanol). All these compounds have reasonably high fluorescence quantum yields (between 16 and 85%) and show different solvent sensitivity in their fluorescence emission. These results indicate that the indole derivatives prepared are good candidates for fluorescent probes. The response of the new synthesised compounds towards fluoride ion (F–) was evaluated. It was found that methyl 3-methyl- 1H-dibenzo[e,g]indole-2-carboxylate, methyl 3-(phenanthren-9-yl)-1H-dibenzo[e,g]indole-2-carboxylate and methyl 1-(naphthalen-1-yl)-3H-benzo[e]indole-2-carboxylate showed significant spectral changes in fluorescence emission upon F– addition with a decrease in intensity and the appearance of a new band at longer wavelengths. No detectable emission spectral changes were observed when several other anions were added to these compounds, which indicates their selectivity towards F-.
TypeArticle
URIhttp://hdl.handle.net/1822/11743
DOI10.1002/ejoc.200900737
ISSN1434-193X
Peer-Reviewedyes
AccessOpen access
Appears in Collections:CDF - FAMO - Artigos/Papers (with refereeing)
CDQuim - Artigos (Papers)

Files in This Item:
File Description SizeFormat 
EurJOC2010 interacção Fluor.pdfDocumento principal1,28 MBAdobe PDFView/Open
EurJOC2010_Fluor supporting info.pdfSupporting Information279,73 kBAdobe PDFView/Open

Partilhe no FacebookPartilhe no TwitterPartilhe no DeliciousPartilhe no LinkedInPartilhe no DiggAdicionar ao Google BookmarksPartilhe no MySpacePartilhe no Orkut
Exporte no formato BibTex mendeley Exporte no formato Endnote Adicione ao seu ORCID