Funkcionalizacija poroznih polimernih monolitov s cinhonidinom preko tiol/en klik reakcij

magistrsko delo

Rene Gole (Author), Peter Krajnc (Mentor), Amadeja Koler (Co-mentor)

Abstract

Namen tega magistrskega dela je bila sinteza poroznega monolitnega materiala na osnovi divinil benzen/vinilbenzil klorida, ki ga bo odlikovala visoka specifična površina, odprto celična morfologija in hierarhična distrubucija velikosti por, površina pa bo primerna za funkcionalizacijo s cinhonidinom. Visoko porozen poli(divinil benzen-ko-vinilbenzil klorida) smo pripravili s polimerizacijo kontinuirne faze emulzije z visokim deležem notranje faze (poliHIPE). Za sintezo smo uporabili nizke začetne stopnje zamreženja (3 mol% in 8 mol% divinil benzena). Nadalje smo poliHIPE materiale hiperzamrežili z reakcijo Friedel-Craftsovega alkiliranja in s tem polimerom drastično zvišali specifično površino in kompatibilnost površine s topili. Na klorometilne skupine, ki se tekom hiperzamreženja niso pretvorile v metilenske povezave, smo vezali cisteamin preko nukleofilne substitucije. Vezava cisteamina je nato omogočila vezavo ciljne kiralne molekule – cinhonidina, preko tiol/en klik reakcije dvojne vezi cinhonidina in proste tiolne skupine cisteamina. Rezultati elementne analize so pokazali na uspešnost vezave cinhonidina na predhodno funkcionalizirane poliHIPE materiale in sicer 0,94 mmol/gpolimer v najboljšem primeru. Taki material bi lahko uporabili kot kiralno kolono. Specifične površine materialov smo določili z adsorpcijo/desorpcijo dušika po B.E.T. metodi, uspešnost funkcionalizacije pa z elementno analizo dušika in žvepla. Morfološke lastnosti polimerov smo okarakterizirali z vrstično elektronsko mikroskopijo.

Keywords

poliHIPE;hiperzamreženje;cisteamin;cinhonidin;kiralne kolone;magistrske naloge;

Data

Language:	Slovenian
Year of publishing:	2021
Typology:	2.09 - Master's Thesis
Organization:	UM FKKT - Faculty of Chemistry and Chemical Engineering
Publisher:	[R. Gole]
UDC:	678.685.82.091.3(043.2)
COBISS:	80880899
Views:	346
Downloads:	65
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	English
Secondary title:	Cinhonidine functionalization of porous polymer monoliths by thiol/ene chemistry
Secondary abstract:	In this master's degree, we adressed the synthesis of a porous divinylbenzene/vinylbenzyl chloride monolith with high specific surface area, opened-cell morphology and hierarchical distribution of pore size, with a surface that offers the option of chemical functionalization with cinchonidine. Highly porous poli(divinylbenzene – co – vinylbenzyl chloride) was synthesised by the polymerization of external phase of high internal phase emulsion (polyHIPE). Low degree of the crosslinker was used (3 mol% and 8 mol% of divinyl benzene). PolyHIPE was then hypercrosslinked by the Frieldel-Crafts alkylation method, which lead to increased specific surface area and increased compatibility with solvents. Methyl chloride groups, which were not used in hypercrosslinking to form methylene crosslinks, served as an entry point for functionalization with cysteamine by the mechanism of nucleophilic substitution. Bonded cysteamine offered the possibility of further functionalization with out target chiral selector – cinchonidine, via a thiol/ene click reaction of cinchonidine double bonds and free thiol groups. Results of elemental analysis show, that cinchonidine was succesfully binded to the prevoiosly functionalized poliHIPE material, with best loading results of up to 0,94 mmol/gpolimer. Prepared material shows promise in chiral separation. Specific surface area was determined by nitrogen adsorbtion via the B.E.T. method. Elemental analysis was used for evaluating the functionalization, specifically sulphur and nitrogen content. The morphology of porous polymers was characterised using scanning electron microscopy.
Secondary keywords:	polyHIPE;hypercrosslinking;cysteamine;cinchonidine;chiral columns;
Type (COBISS):	Master's thesis/paper
Thesis comment:	Univ. v Mariboru, Fak. za kemijo in kemijsko tehnologijo
Pages:	VIII, 61 str.
ID:	13357368