| Abstract | Cilj ovog završnog rada bila je priprava spojeva koji će poslužiti kao prekursori u sintezi novih biomolekulskih fluorescentnih indikatora. Tako je pripravljena serija BODIPY spojeva: 1–3: 4,4-difluor-8-fenil-1,3,5,7-tetrametil-4-bora-3a,4a-diaza-s-indacen (1),
4,4-difluor-8-(4-hidroksifenil)-1,3,5,7-tetrametil-4-bora-3a,4a-diaza-s-indacen (2) i
4,4-difluor-8-fenil-4-bora-3a,4a-diaza-s-indacen (3). Prvi korak u njihovoj sintezi je priprava dipirometana dobro opisanom Lindseyjevom metodom kondezacije pirola s aromatskim aldehidima uz trifluoroctenu kiselinu kao katalizator. Reakcijom 2,4-dimetilpirola (2,4-DMP-a) i benzaldehida ili 4-hidroksibenzaldehida dobiveni su odgovarajući dipirometani (4 i 5). Navedeni dipirometani i 5-fenildipirometan (6), koji je prethodno pripravljen u laboratoriju, prevedeni su in situ u dipirometene uz DDQ (2,3-diklor-5,6-dicijano-1,4-benzokinon) kao oksidans, a kompleksiranjem s borovim trifluoridom kao Lewisovom kiselinom dobivene su ciljne molekule 1–3. Reakcije su provedene u strogo kontroliranim, inertnim uvjetima. Svi sintetizirani spojevi okarakterizirani su spektroskopskim metodama 1H i 13C-NMR, a konačni spojevi 1–3 dodatno još infracrvenom spektroskopijom te određivanjem tališta. |
| Abstract (english) | The aim of this bachelor's thesis was to prepare compounds that would serve as precursors in the synthesis of new biomolecular fluorescent indicators. Thus a series of BODIPY compounds 1–3 was prepared. The first step in their synthesis was the preparation of dipyrromethanes by the well-described Lindsey's condensation of pyrrole with aromatic aldehydes with trifluoroacetic acid serving as a catalyst. The reaction of 2,4-dimethylpyrrole and benzaldehyde or 4-hydroxybenzaldehyde gave the corresponding dipyrromethanes
(4 and 5). These dipyrromethanes, along with 5-phenyldipyrromethane (6) which was previously prepared in the laboratory, were converted in situ to respective dipyrromethenes with DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) as an oxidant and subsequent complexation with boron trifluoride as a Lewis acid afforded target molecules 1–3. Reactions were carried out in strictly controlled conditions. All synthesized compounds were characterized by 1H and 13C-NMR spectroscopic methods, and final compounds 1–3 additionally by infrared spectroscopy and melting point determination. |
