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Sinteza novih polimetinskih fluoroforov iz arilacetonitrilov in etil arilacetatov
Horvat, Maruša (Author), Mravljak, Janez (Mentor) More about this mentor... This link opens in a new window, Pajk, Stane (Co-mentor)

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Abstract
Fluorescenca je oddajanje energije v obliki svetlobe, ki jo je snov pred tem absorbirala. Za organske spojine, ki lahko fluorescirajo, je značilno, da imajo v strukturi več konjugiranih dvojnih vezi (npr. aromatske obroče) – take spojine se imenujejo flourofori. V svojem magistrskem dela je Andraž Bevk nenamenoma izoliral fluorofor, ki je po svoji strukturi še najbolj podoben polimetinom oz. natančneje cianinom. V prvem delu raziskovanja smo poskušali sintetizirati fluorofore s podobnim skeletom. Zanimal nas je vpliv uporabljene izhodne spojine in topila. Kot izhodne spojine smo uporabili arilacetonitrile in etil arilacetate. V primeru obeh so produkti nastali, je pa pri uporabi etil arilacetata prišlo do nadaljnje ciklizacije, vendar je tudi produkt ciklizacije fluoresciral. V nadaljevanju smo poskušali sintetizirati fluorofor iz dveh različnih izhodnih arilacetonitrilov, vendar sinteza v tem primeru ni bila uspešna. Pri sintezah smo uporabili dve različni topili: dimetilformamid in N,N-dimetilacetamid. Pri vseh treh nastalih produktih (spojinah 1, 9 in 13) je bil uporabljen dimetilformamid, ki prispeva ogljikov atom potreben za vezavo dveh izhodnih spojin. Nazadnje smo poskušali fluorofore še alkilirati, saj bi lahko tako nanje vezali različne funkcionalne skupine, a so bili naši poskusi neuspešni. V drugem delu smo za nastale fluorofore (spojine 1, 9 in 13) s pomočjo tekočinske kromatografije ultra visoke ločljivosti določili izkoristek. Najprej smo postavili metodo in izbrali optimalne pogoje ločevanja. Nato smo za vsak produkt določili valovno dolžino, pri kateri sta bili občutljivost in selektivnost metode največji. Pri izbrani valovni dolžini smo posneli kromatograme raztopin produktov z linearnim razponom koncentracij. Pri vsaki koncentraciji smo iz kromatograma odčitali površino pod krivuljo, iz dobljenih podatkov pa smo načrtali graf odvisnosti površine pod krivuljo od koncentracije fluorofora. Pri tem smo dobili enačbo premice, iz katere smo izračunali koncentracijo posameznega produkta in iz tega izkoristek sinteze. Slaba topnost produktov je predstavljala največjo težavo pri določanju izkoristkov. Nazadnje smo za nastale fluorofore posneli še spekter fluorescence. Tip aromatskega sistema ima zagotovo vpliv na ekscitacijski in emisijski spekter, vendar zaradi malega števila pripravljenih spojin še ne moremo dobro opisati razmerja med strukturo in foto-fizikalnimi lastnostmi.

Language:Slovenian
Keywords:fluorescenca, fluorofori, polimetini, cianini, tekočinska kromatografija ultra visoke ločljivosti
Work type:Master's thesis/paper (mb22)
Organization:FFA - Faculty of Pharmacy
Year:2019
Views:409
Downloads:160
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Secondary language

Language:English
Title:Synthesis of novel polymethine fluorophores from arylacetonitriles and ethyl arylacetates
Abstract:
Fluorescence is the energy emitted in the form of light previously absorbed by the substance. The wavelength of the emitted light is longer than the wavelength of the absorbed light. Substances, that have the ability to emit energy in this form, have multiple conjugated double bonds (e.g., aromatic rings) in their structure – called fluorophores. In the course of his master's thesis, Andraž Bevk inadvertently isolated a fluorophore, which in its structure is most similar to polymethine dyes or more accurate to cyanine dyes. In the first part of the study, we tried to synthesize fluorophores from similar skeletons. We were interested in influence of the starting compounds and the solvent. Arylacetonitrile and ethyl arylacetate were used as starting compounds. In both cases, synthesis was successful. In the case, where ethyl arylacetate was used as starting compound, the cyclization of the resulting product, which was also fluorescent, occurred. In the following, we tried to synthesize the fluorophores from two different arylacetonitriles, but the products were not created. Two different solvents were used for the syntheses: dimethylformamide and N,N-dimethylacetamide. For all three resulting products (1, 9, 13), dimethylformamide was used, which is based on the fact, that the carbon atom from dimethylformamide was required to bond the two starting compounds. Lastly, we tried the alkylation of fluorophores, so that we could bind different functional groups onto them. Alkylation was unsuccessful. In the second part, we used ultra-high performance liquid chromatography for determination of synthesis yields of products (1, 9, 13). First, we selected the method and optimal conditions for the separation. Next, we determined a wavelength for each product, where sensitivity and selectivity of the method were the highest. At the selected wavelength, the chromatogram of the product solution with linear range of concentration was recorded. At each concentration, the area under the curve was read from the chromatogram. Next a graph of the dependence of area under the curve from the fluorophore concentration was plotted from the obtained data. A line equation was obtained, from which the concetration and later yield of synthesis of individual products were calculated. Finally, the fluorescence spectrum was recorded. The type of aromatic system certainly has an effect on the excitation and emission spectrum, but due to the small number of compounds prepared, the relationship between structure and photo-physical properties cannot yet be well described.

Keywords:fluorescence, fluorophores, polymethine dyes, cyanine dyes, ultra-high performance liquid chromatography

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