Sinteza i spektroskopska ispitivanja novih benzazolnih derivata kao potencijalnih senzora za pH i metalne katione

undergraduate thesis

• Title (english): Synthesis and spectroscopic evaluation of novel benzazole derivatives as potential sensors for pH and metal cations
• Author: Petra Gurović
• Mentor: Svjetlana Krištafor (mentor)
• Committee member: Svjetlana Krištafor (predsjednik povjerenstva)
• Committee member: Ivana Steinberg (član povjerenstva)
• Committee member: Marijana Hranjec (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2019-07-09, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Derivati benzimidazola pokazuju potencijalnu senzorsku primjenu zbog postojanja slobodnog elektronskog para na dušiku i konjugiranog π-sustava. 1,2,3-triazoli imaju bitnu ulogu u senzorskoj kemiji kao π-poveznica i kao dio fluorofora, a zbog postojanja heteroatoma dušika i dipolnog karaktera mogu sudjelovati u koordinaciji metalnih kationa i stvaranju vodikovih veza. U ovom radu pripravljeni su novi derivati benzimidazola i 1,2,3-triazola reakcijom click kemije iz odgovarajućih aromatskih azida i alkina kao potencijalne senzorske molekule.
Alkin 2-(prop-2-in-1-iltio)-1H-benzo[d]imidazol pripravljen je reakcijom
2-merkapto-benzimidazola s propargil-bromidom, a aromatski azidi reakcijom nukleofilne supstitucije iz odgovarajućeg anilina, odnosno, 4-supstituiranog anilina. Ciljani produkti pripravljeni su 1,3-dipolarnom cikloadicijom azida i alkina uz Cu(I) kao katalizator. Strukture dobivenih spojeva potvrđene su 1H i 13C NMR spektroskopijom. Pripravljenim derivatima dodatno su ispitane spektroskopske karakteristike korištenjem UV-vidljive apsorpcijske i fluorescencijske spektroskopije. Za sve spojeve, snimljeni su apsorpcijski i emisijski spektri u etanolu, a kako bi se ispitala mogućnost primjene spojeva iz pripravljene serije, kao kemosenzorskih molekula za pH ispitana je promjena spektralnih svojstava ovisno o
pH-vrijednosti otopine. Također, za izabrani spoj 10, ispitan je utjecaj prisutnosti različitih metalnih kationa na apsorpcijske spektre.

Abstract (english)

Benzimidazole derivatives have shown potential sensor application due to nitrogen electron pair and conjugated π-system. 1,2,3-triazoles have important role in sensor chemistry as they can act as π-linker, as a part of fluorophore or they could participate in metal coordination an hydrogen bond formation due to nitrogen atoms and dipole character. In this work, novel benzimidazole and 1,2,3-triazole derivatives have been prepared as potential chemosensing molecules using click chemistry approach.
Alkyne 2-(prop-2-yn-1-ylthio)-1H-benzo[d]imidazole was prepared from 2-mercaptobenzimidazole and propargyl bromide, while aromatic azides were synthesised by nucleophilic substitution from corresponding aniline or 4-substituted anilines. Targeted compounds were prepared by 1,3-dipolar azide-alkyne cycloaddition reaction using Cu(I) as catalyst. Structures were confirmed by means of 1H i 13C NMR spectroscopy. UV-visible apsorption and fluorescence spectroscopy were used for investigation of potential sensor application of novel compounds. Apsorption and emission spectra of compounds in ethanol were recorded, while pH and metal sensing potential was tested using UV-visible apsorption spectroscopy.

• Keywords: benzimidazol; click kemija; 1 2 3-triazol; kemosenzor; pH; metalni kationi; spektroskopija
• Keywords (english): benzimidazole; click chemistry; 1 2 3-triazole; chemosensor; pH; metal cations; spectroscopy
• Language: croatian
• URN:NBN: urn:nbn:hr:149:162457
• 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: Chemical Engineering - Undergraduate study; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva (sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Access restricted to students and staff of home institution
• Created on: 2023-05-10 09:33:47