Bis(benztiazolil-triazolil)benzeni kao potencijalne solvatokromne probe

undergraduate thesis

• Title (english): Bis(benzthiazolyl-triazolyl)benzenes as potential solvatochromic probes
• Author: Paola Grobenski
• Mentor: Svjetlana Krištafor (mentor)
• Committee member: Svjetlana Krištafor (predsjednik povjerenstva)
• Committee member: Ivana Steinberg (član povjerenstva)
• Committee member: Danijela Ašperger (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2022-09-19, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom je radu cilj istražiti potencijalnu primjenu bis(benztiazolil-triazolil)benzena kao solvatokromnih proba. Spojevi se sintetiziraju bakrom kataliziranom azid – alkin cikloadicijom (CuAAC) koja se smatra jednom od najzastupljenijih click reakcija. 1,2,3-triazoli primjenjivani su kao kemijski senzori uslijed mogućnosti koordiniranja metalnih iona, te vršenja uloge poveznice u push-pull sustavima. Sintetiziran je 1,4-bis(benztiazolil-triazolil)benzen 3 u niskom iskorištenju. Fotofizička svojstva spoja 3 karakterizirana su UV-vidljivom apsorpcijskom i fluorescencijskom spektrofotometrijom. Ispitan je utjecaj polarnosti otapala na spektre dobivenih spojeva. Korištena otapala su dimetilsulfoksid (DMSO), tetrahidrofuran (THF), aceton, etanol (EtOH), etil-acetat (EtAc), acetonitril, metanol (MeOH), i kloroform. Otapala su birana s obzirom na parametre polarnosti. Uočen je batokromni pomak prilikom otapanja u svim otapalima, te je pri korištenju acetonitrila primijećen Stokesov pomak od 58 nm što spoj čini podobnim za uporabu u svrhu solvatokromne probe. Predložena je modifikacija strukture čime bi se povoljno utjecalo na solvato(fluoro)kromno ponašanje.

Abstract (english)

The objective of this paper has been to explore the potential application of 1,3- and 1,4- bis(benzothiazolyl-triazolyl)benzene as solvatochromic probes. The compounds were synthesized by using copper-catalyzed azide-alkyne cycloaddition (CuAAC), considered to be one of the most common click reactions. 1,2,3-triazoles were used as chemical sensors due to their capacity to coordinate metal ions and serve as a linker in push-pull systems. 1,4-bis(benzothiazolyl-triazolyl)benzene 3 was synthesized in low yield. Photophysical properties of the compound were categorized by using UV-visible absorption and fluorescent spectrophotometry. The influence of solvent polarity on the spectra of synthesized compounds was also examined. Solvents used are as follows: dimethylsulfoxide (DMSO), tetrahydrofurane (THF), acetone, ethanol (EtOH), ethyl-acetate (EtAc), acetonitrile, methanol (MeOH), and chloroform. The solvents were chosen in regard to polarity parameters. A bathochromic shift was observed during the dissolution in all solvents. A Stokes shift of 58 nm was noticed in the case of acetonitrile, which indicates that the compound is suitable for use as a solvato(fluoro)chromic probe. Finally, structural modifications are proposed as they would have a positive influence on solvato(fluoro)chromic behaviour of the compound.

• Keywords: optički kemijski senzori; click kemija; benztiazol 1 2 3-triazol; UV-vidljiva spektrofotometrija; fluorescencija; intramolekularni prijenos naboja
• Keywords (english): optical chemical sensors; click chemistry; benzthiazole 1 2 3-triazole; UV-visible spectrophotometry; fluorescence; intramolecular charge transfer
• Language: croatian
• URN:NBN: urn:nbn:hr:149:841782
• 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: Open access
• Created on: 2023-02-24 08:05:45