Sinteza i separacijska svojstva cirkonijevih homokiralnih metaloorganskih mreža s ligandima izvedenim iz aminokiselina

master's thesis

• Title (english): Synthesis and separation properties of zirconium based homochiral metal-organic frameworks with amino acid derived ligands
• Author: Ivan Lisjak
• Mentor: Nikola Cindro (mentor)
• Committee member: Nikola Cindro (predsjednik povjerenstva)
• Committee member: Iva Juranović Cindrić (član povjerenstva)
• Committee member: Dominik Cinčić (član povjerenstva)
• Committee member: Nikola Bregović (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2023-02-03, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U okviru rada je iz fumarne kiseline u 4 koraka sintetizirana ciklobutan-1,2,3,4-tetrakarboksilna
kiselina (cBTA) na koju su zatim amidnom vezom vezane po 4 molekule različitih
aminokiselina: L-alanina, L-fenilalanina i L-prolina. Dobiveni homokiralni ligandi korišteni su
za pripravu metaloorganskih mreža (MOF-ova) u solvotermalnim i mehanokemijskim
reakcijama sa spojevima cirkonija(IV). Separacijska svojstva MOF-a izvedenog iz L-alanina
ispitana su pomoću tri kiralna organska spoja. Katalitička svojstva istog MOF-a ispitana su na
aldolnoj reakciji cikloheksanona i 4-nitrobenzaldehida. Separacija je praćena tekućinskom
kromatografijom visoke djelotvornosti s kiralnom stacionarnom fazom. Sintetizirani ligandi
analizirani su spektroskopijom NMR, masenom spektrometrijom i IR spektroskopijom. MOFovi su analizirani difrakcijom rentgenskog zračenja na polikristalnom uzorku,
termogravimetrijom, IR spektroskopijom te spektroskopijom NMR u čvrstom stanju.

Abstract (english)

Within this thesis cyclobutane-1,2,3,4-tetracarboxylic acid (cBTA) was synthesised in 4 steps
starting from fumaric acid. Amide bonds were formed between cBTA and 4 molecules of
different amino acids: L-alanine, L-phenylalanine and L-proline. Obtained homochiral ligands
were used to prepare metal-organic frameworks (MOFs) through solvothermal and
mechanochemical reactions with zirconium(IV) compounds. Separation properties of the MOF
derived from L-alanine were investigated using different chiral organic compounds followed by
high performance liquid chromatography with a chiral stationary phase. Catalytic properties of
the MOF were investigated through the aldol reaction of cyclohexanone and
4-nitrobenzaldehyde. Synthesised ligands were analysed using NMR spectroscopy, mass
spectrometry and IR spectroscopy. MOFs were analysed using powder x-ray diffraction,
thermogravimetry, IR and solid-state NMR spectroscopy.

• Keywords: aminokiselina; ciklobutantetrakarboksilna kiselina; cirkonij; enantioselektivna separacija; kiralnost; metaloorganska mreža
• Keywords (english): amino acid; chirality; cyclobutanetetracarboxylic acid; enantioselective separation; metal-organic framework; zirconium
• Language: croatian
• URN:NBN: urn:nbn:hr:217:282751
• Study programme: Title: Graduate university studies in chemistry; specializations in: Research programme; Course: Research programme; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra kemije (magistar/magistra kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Embargoed access; Embargo expiration date: 2025-02-03
• Created on: 2023-02-21 13:54:53