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J Org Chem ; 68(4): 1512-20, 2003 Feb 21.
Artículo en Inglés | MEDLINE | ID: mdl-12585896

RESUMEN

In this paper we report the synthesis of a new class of fluorescent thiophene-based isothiocyanates containing a 3,5-disubstituted dithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide moiety as the rigid core, using the palladium-catalyzed cross-coupling reaction of aryl stannanes with aryl bromides (Stille coupling). By changing the molecular structure through the progressive addition of thienylene or phenylene units, light emission from blue to orange was obtained. Photoluminescence quantum yields ranged from 0.65 to 0.90 for blue and green light emitters to 0.10-0.35 for yellow and orange ones. Optically and chemically stable fluorescent bioconjugates were prepared by spontaneous reaction of the isothiocyanates with monoclonal antibodies anti-CD3 and anti-CD8 in slightly basic solutions.


Asunto(s)
Anticuerpos Monoclonales/química , Colorantes Fluorescentes/síntesis química , Isotiocianatos/síntesis química , Tiofenos/síntesis química , Complejo CD3/inmunología , Antígenos CD8/inmunología , Catálisis , Colorantes Fluorescentes/química , Inmunoconjugados/química , Isotiocianatos/química , Estructura Molecular , Espectrometría de Fluorescencia , Estereoisomerismo , Tiofenos/química
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