Sinteza, karakterizacija i tautomerija nove azo boje na bazi orotične kiseline
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http://orcid.org/0000-0003-4945-7776
Vojkan Stamenković
Jelena Lađarević
http://orcid.org/0000-0002-5554-7295
Nemanja Trišović
http://orcid.org/0000-0002-9231-4810
Anita Lazić
http://orcid.org/0000-0003-4855-3782
Aleksandra Mašulović
http://orcid.org/0000-0002-5279-7694
Dušan Mijin
http://orcid.org/0000-0001-5691-2971
Apstrakt
Sinteza azo boja koje u svojoj strukturi sadrže heterociklična jedinjenja postala je predmet sve većeg interesovanja poslednjih godina, prvenstveno zbog širokog spektra bioloških i farmakoloških aktivnosti ovih jedinjenja. Pored ovoga, heterociklične azo boje nalaze primenu kao fluorescentni materijali, nelinearni optički (NLO) materijali drugog reda, kao i komponente tečnih kristala. Takođe, uvođenje heterocikličnih jedinjenja u moleklule azo boja omogućava modifikaciju njihovih elektronskih i optičkih svojstava, čime se povećava intenzitet boje i poboljšava efikasnost bojenja. Značajnu podklasu heterocikličnih jedinjenja predstavljaju derivati pirimidina koji ispoljavaju raznovrsna fiziološka i biološka svojstva. Orotična kiselina (vitamin B13) ima ključnu ulogu u biosintezi pirimidina i često se uključuje u formulacijama dijetetskih suplemenata i multivitamina. Orotična kiselina takođe nalazi primenu u raznim jonoizmenjivačkim procesima, očuvanju hrane, a koristi se i kao biokatalizator u medicini. U ovom radu prikazana je sinteza i detaljna karakterizacija nove azo boje dobijene iz 5-aminoorotične kiseline. Ova azo boja je sintetizovana konvencionalnim reakcijama diazotovanja i diazo-kuplovanja, a okarakterisana je temperaturom topljenja, ATR-FTIR i 1H NMR spektroskopijom. Da bi se ispitala veza između molekulske strukture i optičkog svojstva sintetizovanog jedinjenja, sprovedena je solvatohromna analiza u setu rastvarača različite polarnosti. Pored toga, UV-Vis spektroskopijom je ispitana zavisnost tautomerne ravnoteže od pH vrednosti rastvarača (kiselo-bazna ravnoteža).
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