20.500.12556/DKUM-45623 POLIMERNO VEZANI OKSALATI KOT OBNOVLJIVI VIRI KEMILUMINISCENCE POLYMER BOUND OXALATES AS RENEWABLE SOURCES OF CHEMILUMINESCENCE V diplomskem delu smo raziskali možnosti sinteze derivatov diaril oksalatnih estrov vezanih na polimerne nosilce. Diaril oksalati so zanimive spojine za kemiluminiscenčne reakcije, saj pri reakciji z vodikovim peroksidom nastane visoko-energijska molekula, ki se ob prisotnosti primernega občutljivca pretvori v osnovno stanje s sevanjem svetlobe. Arilni del molekule pomembno vpliva na kemiluminiscenčne lastnost, zato smo raziskali možnosti vezave elektron-privlačne skupine, kot je brom, ki bi podaljšal čas oddajanja svetlobe. Raziskali smo, kakšne so možnosti v strukturi arilnega dela molekule, da bi lahko omogočila pripravi diaril oksalatov na trdnih nosilcih. Ugotovili smo, da mora benzenski del molekule vsebovati fenolno skupino, preko katere se lahko veže oksalatna skupina ter aminsko skupino, ki bi služila za vezavo na benzilno mesto v polimernem nosilcu. Iz tega razloga smo raziskali reakcijo bromiranja 4-metoksibenzilamina in 4-hidroksibenzonitrila z okolju sprejemljivejšo metodo oksidativnega bromiranja z bromovodikovo kislino in vodikovim peroksidom kot oksidantom v različnih topilih pod različnimi pogoji. Nadalje smo raziskali reakcijo vezave na polimerni nosilec in kot modelno spojino uporabili benzil klorid, na katerega smo vezali benzilaminski derivat. V zadnjem koraku svojega raziskovanja, sem pozornost posvetila raziskovanju reakcije vezave oksalatne skupine na fenolni derivat kot modelno reakcijo za uporabo na polimernem nosilcu. S tem smo pripravili metodo, s katero lahko apliciramo kemiluminiscenco v trdni fazi, npr. PoliHIPE polimer. Z vezavo fenola v PoliHIPE polimer bi dobili obnovljivi vir kemiluminiscence, saj bi lahko fenol na ta način enostavno regenerirali v diariloksalatni ester in edini stranski produkt bi bil ogljikov dioksid. In the thesis, we explore the synthesis of derivatives of diaryl oxalate esters linked on polymer supports. Diaryl oxalates are interesting compounds for the chemiluminescent reaction, because the reaction with hydrogen peroxide formed high-energy molecule which, in the presence of a suitable fluorophore converted into the ground state by radiation of light. Aryl moiety significant impact on the chemiluminescent property, so we researched the possibility of binding an electron-attractive group such as bromine, which would extend the time for light emission. We explored the possibilities in the structure of the aryl moiety that could allow the preparation of diaryl oxalates on solid supports. We found out that the benzene moiety includes the phenolic group by means of which can bind oxalate group and an amine group that would serve to bind to the benzyl position in the polymer carrier. For this reason, we studied the bromination reaction of 4-methoxybenzylamino, and 4-hydroxybenzonitrile with environmentally more acceptable method of oxidative bromination with hydrobromic acid and hydrogen peroxide as an oxidant in different solvents under different conditions. Furthermore, we studied the binding reaction on a polymeric carrier, and as a model compound using benzyl chloride, to which was bound the benzyl derivative. In the last step of my research, I pay special attention to exploring fixation oxalate groups on the phenolic derivative as a model reaction for use in the polymer carrier. In this way we have prepared a method which can chemiluminescent solid phase be applied, eg. PolyHIPE polymer. The binding of phenol in the polymer PolyHIPE to get a renewable source of chemiluminescence, as it could phenol in this way easily regenerate in diariloksalatni ester and the only byproduct would be carbon dioxide. kemiluminiscenca diariloksalatni estri reagenti na trdnih nosilcih PoliHIPE chemiluminescence diaryl oxalate esters reagents on solid supports polyHIPE true true false [S. Bošnjak] Slovenski jezik Angleški jezik Diplomsko delo/naloga 2014-08-30 12:00:06 2014-09-22 20:31:18 2022-05-16 03:05:50 2021-05-02 03:31:57 2014 0 Maribor 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 547.461.2.057:535.379(043.2) 18131990 URN:SI:UM:DK:ZHMXSTSB UNI_Bosnjak_Selena_2014.pdf UNI_Bosnjak_Selena_2014.pdf 1 0470F449559FE70F7BC9030B04E9814F 9d33edb93f12685ce13e3f2f4293507fd902590aca20f9d25765b0918099e317 3a6521bf-7c0b-11eb-bb7a-00155d0001ca https://dk.um.si/Dokument.php?lang=slv&id=67199 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0