Fluorescentni pi-konjugirani heterociklički kemosenzori temeljeni na 1,2,3-triazolu: sinteza i optička svojstva

master's thesis

• Title (english): Fluorescent pi-conjugated heterocyclic chemosensors based on 1,2,3-triazole ring: synthesis and optical properties
• Author: Matej Perković
• Mentor: Svjetlana Krištafor (mentor)
• Committee member: Svjetlana Krištafor (predsjednik povjerenstva)
• Committee member: Ivana Steinberg (član povjerenstva)
• Committee member: Tatjana Gazivoda Kraljević (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2015-07-09, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Applied Chemistry

Abstract

Cilj ovog rada je sinteza i optička karakterizacija novih derivata benzazola (benzimidazola, benzotiazola i benzoksazola) koji sadrže triazolnu jezgru radi utvrđivanja potencijalne senzorske primjene. Spojevi 4 i 5 uspješno su sintetizirani reakcijama klasične organske sinteze i click reakcijom terminalnog alkina i azida. Strukture svih priređenih spojeva potvrđene su spektroskopskom metodom 1H-NMR.
Ispitivani spojevi su okarakterizirani pomoću UV-vidljive apsorpcijske i fluorescencijske spektrofotometrije na promjenu vrijednosti pH u univerzalnom puferu u rasponu od 1,02 do 12,02. Eksperimentalno je određen utjecaj otapala različitih parametara polarnosti na spektralna svojstva ispitivanih spojeva. Ispitan je i utjecaj različitih metalnih iona na intenzitet fluorescencije spojeva u otopinama.
Spektrofotometrijskom karakterizacijom u otopinama spojeva utvrđeno je da ispitivani spojevi pokazuju mogućnost primjene kao optički pH senzori u kiselom mediju.
Kod spojeva 4 i 5 uočen je solvatokromizam.
Uočena je promjena spektrofotometrijskih svojstava u prisutnosti metalnih iona. Spojevi 4 i 5 pokazuju mogućnost upotrebe kao senzori za metale.

Abstract (english)

Aim of this work was synthesis and optical characterisation of novel benzazole derivatives (benzimidazole, benzthiazole, benzoxazole) based on triazole linker, in order to determine their potential sensor applications. Compounds 4 and 5 were successfully synthesized by reactions of classical organic synthesis and click reaction with terminal alkyne and azide. The structures of all synthesized compounds were confirmed by 1H-NMR spectroscopy.
Compounds were characterized by UV-Visible absorption and fluorescence spectrophotometry in the universal buffer solutions in the pH range 1,02 to 12,02. The effect of solvent polarity was also studied. The influence of various metal ions on the fluorescence spectra was examined in solutions.
By spectrophotometric characterization studies of the solution was found that tested compounds could have potential application as optical pH sensors in an acidic medium.
Compounds 4 and 5 showed solvatochromism.
Change in the spectroscopic properties due to the presence of metal ions was detected, so the compounds 4 and 5 are suitable for potential metal sensing applications.

• Keywords: kemosenzori; fluorescencija; triazoli; click kemija
• Keywords (english): chemosensors; fluorescence; triazoles; click chemistry
• Language: croatian
• URN:NBN: urn:nbn:hr:149:402538
• Study programme: Title: Applied Chemistry - Graduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry; Course: Applied organic chemistry; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2016-12-07 14:22:01