20.500.12556/DKUM-90730 Funkcionalizacija hidrokinonskih obročev z okso-nukleofilnimi substitucijami za pripravo konjugiranih polielektrolitov Functionalization of hydroquinone rings by oxo-nucleophilic substitutions for the preparation of conjugated polyelectrolytes Diplomska naloga je kombinacija organske sinteze, polimerne kemije in organske analize. Izvedli smo sintezo malih molekul, ki služijo kot prekurzorji za pripravo konjugiranih polielektrolitnih (CPE) polimerov. Prekurzorje, 3,3'-((2,5-dibromo-1,4-fenilen)bis(okso))bis(N,N,N-trimetilpropan-1-aminijev) bromid, 3,3'-((2,5-dietinill-1,4-fenilen)bis(oksi))bis(N,N,N-trimetilpropan-1-aminijev) bromid in 3,3'-((2,5-diformil-1,4-fenilen)bis(okso))bis(N,N,N-trimetilpropan-1-aminijev) bromid smo pripravili z okso-nukleofilno substitucijo, natančneje, izvedli smo t. i. Williamsovo eintezo etra. Prekurzor 1,3,5-tris(4-bromofenil)benzen, smo sintetizirali s kislinsko katalizirano aldolno kondenzacijo, pri kateri nastane trimerna spojina. Tako pripravljene prekurzorje, smo v nadaljevanju uporabili za pripravo CPE z reakcijami Sonogashira-Hagihara in Suzuki-Miyaura navzkrižnim pripajanjem ter s Schiff-bazno reakcijo. Monomere in polimere smo analizirali z uporabo 1H NMR spektroskopije (prekurzorji), FTIR spektroskopije (polimeri), DRS UV-Vis spektroskopije (polimeri) in CHN elementne analize (prekurzorji in polimeri). Uspešno smo izvedli sintezo treh prekurzorjev in dveh CPE polimerov. Strukturo prekurzorjev smo potrdili z 1H NMR. Strukturo polimerov smo potrdili z FTIR spektroskopijo. Z DRS UV-Vis smo polimeroma določili optične lastnosti. Rezultati elementne analize dopolnjujejo NMR in FTIR rezultate in potrjujejo željene molekule in makromolekule. The diploma thesis is a combination of organic synthesis, polymer chemistry and organic analysis. We have carried out the synthesis of small molecules that serve as precursors for the preparation of conjugated polyelectrolyte (CPE) polymers. The precursors, 3,3'-((2,5-dibromo-1,4-phenylene)bis(oxy))bis(N,N,N-trimethylpropane-1-aminium)bromide, 3,3'-((2,5-diethynyl-1,4-phenylene)bis(oxy))bis(N,N,N-trimethylpropane-1-aminium)bromide, and 3,3'-((2,5-diformyl-1,4-phenylene)bis(oxy))bis(N,N,N-trimethylpropan-1-aminium)bromide were prepared by oxo-nucleophilic substitution, namely by carrying out the so-called Williamson ether synthesis. The precursor, 1,3,5-tris(4-bromophenyl)benzene, was synthesized by acid-catalyzed aldol condensation, resulting in a trimeric compound. These precursors were subsequently used to prepare CPEs by Sonogashira-Hagihara and Suzuki-Miyaura cross-coupling reactions and by a Schiff base reaction. The monomers and polymers were analyzed by ¹H-NMR spectroscopy (precursors), FTIR spectroscopy (polymers), DRS-UV-Vis spectroscopy (polymers) and CHN elemental analysis (precursors and polymers). Finally, we successfully synthesized three precursors and two CPE polymers. The structure of the precursors was confirmed by ¹H NMR. The structure of the polymers was confirmed by FTIR spectroscopy. The optical properties of the polymers were determined by DRS-UV-Vis spectroscopy. The results of the elemental analysis complement the NMR and FTIR spectroscopy analysis and confirm the desired molecules and macromolecules. Williamsova sinteza etra Sonogashira-Hagihara reakcija Suzuki-Miyaura reakcija Schiff-bazna reakcija konjugirani polielektrolitni polimeri Williamson ether synthesis Sonogashira-Hagihara reaction Suzuki-Miyaura reaction Schiff base reaction conjugated polyelectrolyte polymers (CPE) true true false [M. Šilak] Slovenski jezik Angleški jezik Diplomsko delo/naloga 2024-09-18 10:55:06 2024-10-15 14:32:59 2025-01-10 08:32:56 0000-00-00 00:00:00 2024 0 Maribor 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 544.6.018.47-036.5(043.2) 221670659 UN_Silak_Matej_2024.pdf UN_Silak_Matej_2024.pdf 1 00B520B2494A6EF218DFEC5DA6CC161D 5ddd7717e270aa5b7012aee335344771a6c331b6137d602e8c35f1889e907fb4 e03a1f44-cdb6-11ef-9362-00155d000105 https://dk.um.si/Dokument.php?lang=slv&id=187688 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0