Sinteza i spektroskopska karakterizacija novih 1,2,3-triazolnih derivata benztiazola

undergraduate thesis

• Title (english): Synthesis and spectroscopic characterization of novel 1,2,3-triazolylbenzothiazoles
• Author: Jakov Tenžera
• Mentor: Lidija Furač (mentor)
• Committee member: Lidija Furač (predsjednik povjerenstva)
• Committee member: Svjetlana Krištafor (član povjerenstva)
• Committee member: Matija Cvetnić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2020-09-23, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

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.

Abstract (english)

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.

• Keywords: ˝click˝ kemija; benztiazol; derivati benztiazola; 1 2 3-triazol; kemosenzor; spektroskopija; pH senzor
• Keywords (english): ˝click˝ chemistry; benzothiazole; benzothiazole derivatives; 1 2 3-triazole; chemosensor; spectroscopy; pH sensor
• Language: croatian
• URN:NBN: urn:nbn:hr:149:719072
• Project: Number: IP-2014-09-3386; Title: Dizajn i sinteza novih dušikovih heterocikličkih fluorofora i fluorescentnih nanomaterijala kao kemijskih senzora za pH i metalne ione; Title: Design and Synthesis of Novel Nitrogen-Containing Heterocyclic Fluorophores and Fluorescent Nanomaterials for pH and Metal-Ion Sensing; Acronym: iNFiNiTE–SENS; Leader: Robert Vianello; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• Study programme: Title: Applied Chemistry - Undergraduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry; Course: Advanced materials and technologies; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2023-05-09 09:05:07