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Synthesis of New Triazolopyridine and Triazoloquinoline Based Ligands and Application as Fluorescence Sensors

出版	2009
URL	http://books.google.com.hk/books?id=t70LmwEACAAJ&hl=&source=gbs_api

註釋The present PhD manuscript concerns the chemistry of triazolopyridines and triazoloquinolines. We have synthesized the first chiral triazolopyridines opening an easy access to 2,6-disubstituted chiral pyridines. We have also extended a methodology of palladium catalysed sulfenation to different heterocyclic aromatic compounds. Secondly, by restudying the chemistry of the [1,2,3]triazolo[1,5-a]quinoline we have proposed a new access to 2,8-disubstitued quinolines. The ring chain isomerisation of the triazoloquinoline-pyridine system has been studied and we have used this isomerisation to obtain high fluorescent structures able to recognize copper. In the course of our studies we have employed the properties of triazolopyridines to quantify the electronic profile of phosphines as well as to prepare a new generation of triazolopyridine-phosphine based ligands for catalysis. The analysis of these structures has allowed us to observe the special properties associated to the phosphorus lone pair in the electronic profile and also in the 13C-NMR-spectra. Finally, we have been able to prepare many different fluorescence receptors, and we have studied them, some of these compounds have revealed as excellent zinc sensors, as well as for some anions and as for amino acids. Finally, we have been able to perform chiral recognition employing a zinc complex based on our fluorophor and L-histidine as chiral compound.