Please use this identifier to cite or link to this item: http://hdl.handle.net/1822/23329

TitleNew 1,3-diarylureas linked by C-C Suzuki coupling to the methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate moiety: synthesis and fluorescence studies in solution and in lipid membranes
Author(s)Queiroz, Maria João R. P.
Peixoto, Daniela
Rodrigues, Ana Rita O.
Mendes, Pedro M. F.
Costa, Cátia N. C.
Coutinho, Paulo J. G.
Castanheira, Elisabete M. S.
Keywords1,3-Diarylureas
Thieno[3,2-b]pyridines
Fluorescence
Lipid membranes
Fluorescence probes
Issue dateMar-2013
PublisherElsevier
JournalJournal of Photochemistry and Photobiology a : Chemistry
Abstract(s)New six fluorescent 1,3-diarylureas linked by C-C Suzuki coupling to the 6-position of the methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate moiety were prepared by reaction of the amino groups on the ortho or meta positions relative to the C-C bond of the Suzuki coupling products, with different para-substituted arylisocyanates (H, OMe, CN), in high to excellent yields. The fluorescence properties of the 1,3-diarylureas in solution and in lipid membranes of egg-yolk phosphatidylcholine (Egg-PC), dipalmitoyl phosphatidylcholine (DPPC), dipalmitoyl phosphatidylglycerol (DPPG) or dioctadecyldimethylammonium bromide (DODAB), with or without cholesterol (Ch), were studied. The six 1,3-diarylureas have reasonable fluorescence quantum yields in several solvents (between 0.02 and 0.69) and present a moderately solvent sensitive emission, but are not fluorescent in alcohols and water. The compounds bearing the arylurea moiety in the meta position relative to the C-C bond, especially with the OMe and CN substituents, present the better solvatochromic properties. Incorporation of the six compounds in lipid membranes indicates that all the compounds are deeply located in the hydrophobic region of the lipid bilayers, feeling the transition between the rigid gel phase and fluid phases.
TypeArticle
URIhttp://hdl.handle.net/1822/23329
DOI10.1016/j.jphotochem.2013.01.006
ISSN1010-6030
Publisher versionwww.sciencedirect.com
Peer-Reviewedyes
AccessOpen access
Appears in Collections:CDF - FAMO - Artigos/Papers (with refereeing)
CDQuim - Artigos (Papers)

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