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Synthesis and investigation of morphological, electrochemical, and antioxidative properties of tethered bis-pyrrolidino derivatives of fullerene c60

dc.contributor.advisorMilić, Dragana
dc.contributor.otherTomović, Željko
dc.contributor.otherŠolaja, Bogdan
dc.contributor.otherBjelaković, Mira
dc.contributor.otherMaslak, Veselin
dc.creatorKop, Tatjana J.
dc.date.accessioned2016-08-21T07:07:27Z
dc.date.available2016-08-21T07:07:27Z
dc.date.available2020-07-03T10:14:03Z
dc.date.issued2016-03-07
dc.identifier.urihttp://eteze.bg.ac.rs/application/showtheses?thesesId=3639
dc.identifier.urihttp://nardus.mpn.gov.rs/handle/123456789/6283
dc.identifier.urihttps://fedorabg.bg.ac.rs/fedora/get/o:12423/bdef:Content/download
dc.identifier.urihttp://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=48013327
dc.description.abstractDerivati fulerena C60, zahvaljujući svojim jedinstvenim fizičkohemijskim i elektronskim svojstvima, koja proističu iz visoko konjugovanog π-sistema, čine zanimljive gradivne elemente u sintezama složenijih ciljnih molekula. Različitim derivatizacijama hidrofobne ugljenične sfere dobija se niz proizvoda primenljivih u hemiji materijala, supramolekulskoj i medicinskoj hemiji. Imajući u vidu povećanje rastvorljivosti, kao i promenu stereoelektronskih osobina sa povećenjem broja adenada na fulerenskom jezgru, korisna je svaka metoda višestruke derivatizacije fulerena koja se odigrava pod kontrolisanim uslovima. Prato-va reakcija jedan je od najzastupljenijih vidova kovalentne modifikacije fulerena. U njoj nastaju fuleropirolidini, proizvodi jasno definisane strukture i česti intermedijeri u složenim hemijskim tranformacijama fulerena. Ozbiljno ograničenje ove reakcije predstavlja lako i neselektivno građenje bis- i tris-pirolidinskih adukata, koji značajno umanjuju prinose i čistoću monoadukata. S druge strane, bisadukti su se pokazali korisnima u nekim sferama medicinske hemije i elektrohemije. Regioselektivno dobijanje bisadukata fulerena upotrebom posebno dizajniranih premošćenih supstrata bio je predmet interesovanja nekolicine istraživačkih grupa u proteklom periodu. U toku ovog rada sintetisan je niz alkil-premošćenih diglicina, u cilju dobijanja premošćenih bis-pirolidinskih adukata fulerena u reakciji dvostruke Prato-ve cikloadicije. U prvom delu rada, na supstratu premošćenom oktametilenskim nizom, optimizovani su reakcioni uslovi za dobijanje bisadukata. Optimalnim reakcionim uslovima podvrgnuti su i ostali supstrati, premošćeni alkil-nizovima dužine od 6 do 12 C-atoma i utvrđena je zavisnost regioselektivnosti od dužine niza. Istim reakcionim uslovima podvrgnuta su i dva supstrata koji sadrže dve, odnosno tri etarske podstrukture u mostu i ispitan je uticaj kiseonikovih atoma u linkeru na selektivnost reakcije...sr
dc.description.abstractDue to their unique physicochemical and electronic properties, emerging from highly conjugated π-system, derivatives of the fullerene C60 are interesting building blocks in the synthesis of the more complex target molecules. Diverse derivatizations of hydrophobic carbone sphere provide a wide range of products for the use in matherial, supramolecular and medicinal chemistry. Since the increase of the number of addends on the carbon core improves the solubility and varies the stereoelectronic properties, each method of the controlable multiple derivatization of fullerenes is highly useful. Prato's reaction is one of the most common methodes for the covalent modification of fullerenes. The fulleropyrrolidines, products with well defined structures, are frequently used as intermediers in further chemical transformations of fullerenes. This reaction is limited with the easy and unselective formation of bis- and tris(pyrrolidino) adducts and, hence, decrease of the yields and the purity of monoadducts. On the other hand, bisadducts are very useful in some aspects of the medicinal and electrochemistry. During the recent period, the regioselective synthesis of the fullerene bisadducts via templated supstrates has been the topic of interest of several researcher groups. In this work, a series of alkyl-tethered diglycines were synthesized and underwent the Prato's biscycloaddition conditions in aim to obtain templated bis(pyrrolidino)fullerenes. The first part of the work refers to the optimization of the biscycloaddition conditions on the octamethylene-tethered substrate. Other diglycines, wearing from C6 to C12 alkyl-linkers, were subjected to this optimal reaction conditions and the correlation between the distribution of the regioisomers and the lenght of the linker is determined. Another two diglycines, wearing two and three oxygen atoms in the tether, underwent the same reaction conditions in aim to investigate the influence of the etheric subunits on the selectivity of the reaction...en
dc.formatapplication/pdf
dc.languagesr
dc.publisherУниверзитет у Београду, Хемијски факултетsr
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172002/RS//
dc.rightsopenAccessen
dc.sourceУниверзитет у Београдуsr
dc.subjectfuleren C60sr
dc.subjectFullerene C60en
dc.subjectbis(pirolidino)fulerensr
dc.subjectregioselektivnost biscikloadicijesr
dc.subjectciklična voltametrijasr
dc.subjectSEMsr
dc.subjectfulerozomisr
dc.subjectantioksidativna aktivnostsr
dc.subjectFOXsr
dc.subjectbis(pyrrolidino)fullereneen
dc.subjectbiscycloaddition regioselectivityen
dc.subjectcyclic voltammetryen
dc.subjectSEMen
dc.subjectfullerosomesen
dc.subjectantioxidant activityen
dc.subjectFOXen
dc.titleSinteza i ispitivanje morfoloških elektrohemijskih i antioksidativnih osobina premošćenih bis-pirolidinskih derivata fulerena C60sr
dc.titleSynthesis and investigation of morphological, electrochemical, and antioxidative properties of tethered bis-pyrrolidino derivatives of fullerene c60en
dc.typedoctoralThesis
dc.rights.licenseBY-NC-SA
dcterms.abstractМилић, Драгана; Томовић, Жељко; Шолаја, Богдан; Бјелаковић, Мира; Маслак, Веселин; Коп, Татјана Ј.; Синтеза и испитивање морфолошких електрохемијских и антиоксидативних особина премошћених бис-пиролидинских деривата фулерена Ц60; Синтеза и испитивање морфолошких електрохемијских и антиоксидативних особина премошћених бис-пиролидинских деривата фулерена Ц60;
dc.identifier.fulltexthttp://nardus.mpn.gov.rs/bitstream/id/29666/Kop_Tatjana_J.pdf
dc.identifier.fulltexthttp://nardus.mpn.gov.rs/bitstream/id/29665/Disertacija4288.pdf


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