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Derivati benztiazola pokazuju potencijalnu senzorsku primjenu zbog postojanja slobodnog elektronskog para na dušiku i konjugiranog π-sustava u benztiazolnom prstenu. 1,2,3-triazoli imaju bitnu ulogu u senzorskoj kemiji kao fluorofor i kao π-poveznica, a zbog postojanja heteroatoma dušika te dipolnog karaktera mogu sudjelovati u koordinaciji metalnih kationa i stvaranju vodikovih veza. Cilj rada je korištenjem ˝click˝ reakcije pripraviti novi derivat benztiazola i 1,2,3-triazola iz odgovarajućih aromatskih azida i alkina kao potencijalna senzorska molekula. Ciljani produkt pripravljen je 1,3-dipolarnom cikloadicijom azida i alkina uz Cu(I) kao katalizator. Struktura dobivenog spoja potvrđena je 1H-NMR i 13C-NMR spektroskopijom. Nadalje, provedena su preliminarna ispitivanja sintetiziranog 2-(4-(tiofen-3-il)-1H-1,2,3-triazol-1-il)benzo[d]tiazola (2) kao kemosenzora korištenjem UV-vidljive i fluorescencijske spektroskopije. Ispitane su spektralne karakteristike novog spoja u otapalima različite polarnosti te u univerzalnim puferima u rasponu pH vrijednosti 2-12, te otopini HCl pH=1 i NaOH pH=13. Benzothiazole derivatives show potential sensory application due to the free electron pair on nitrogen atom and conjugated π-system in benzthiazole moiety. 1,2,3-triazoles play an important role in sensor chemistry as fluorophore and as π-linker. Because of nitrogen hetero atoms and dipole character, triazoles can participate in the coordination of metal cations and in the formation of hydrogen bonds. The aim of this work is to prepare a new benzothiazole and 1,2,3-triazole derivative from the corresponding aromatic azides and alkynes as potential sensory molecules by ˝click˝ reactions. The target product was prepared by 1,3-dipolar cycloaddition of azides and alkynes with Cu(I) as a catalyst. The structure of the obtained compound was confirmed by means of 1H-NMR and 13C-NMR spectroscopy. Furthermore, the potential use of synthesized 2-(4-(thiophen-3-yl)-1H-1,2,3-triazol-1-yl) benzo[d]thiazole (2) as a chemosensor was examined using UV-visible absorption and fluorescence spectroscopy. Spectral characteristics of compound were examined in solvents of different polarity and in universal buffer solutions in the pH range 2-12, HCl solution pH=1 and NaOH solution pH=13. |
