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U cilju proučavanja utjecaja piridinske jezgre kao supstituenta na fotokemijsko ponašanje konjugiranih distilbenskih sustava, Wittigovom reakcijom sintetiziran je 1,2-bis(2-(piridin-2-il)vinil)benzen kao smjesa geometrijskih izomera. Iz smjese geometrijskih izomera uspješno su izolirani 2-[(E)-2-{2-[(E)-2-(piridin-2-il)etenil]fenil}etenil]piridin i 2-[(Z)-2-{2-[(E)-2-(piridin-2-il)etenil]fenil}etenil]piridin. Novosintetizirani derivat podvrgnut je fotokemijskim reakcijama na 300 nm i 350 nm u smislu priprave novih distilbenskih struktura fotokemijskom metodologijom. Početni spojevi pokazali su različita fotokemijska svojstva. Fotokemijska reakcija spoja 1,2-bis(2-(piridin-2-il)vinil)benzena (1') dovodi do stvaranja dimernog produkta, 1,2,3,4-tetra(piridin-2-il)ciklobutana (3'), također nastali su i neki novi intermedijari koje nismo uspjeli izolirati kromatografski jer su nestabilni i raspadaju se. Polazni spoj, kao i fotokemijski produkt okarakterizirani su modernim spektroskopskim metodama (jednodimenzionalni i dvodimenzionalni NMR, UV/VIS spektroskopijom). For the purpose of studying the impact of the pyridine base as a substituent on the photochemical behavior of conjugated distilbene systems 1,2-bis(2-(piridine-2-il)vinyl)benzene (1’) has been synthesized using Wittig's. 2-[(E)-2-{2-[(E)-2-(pyridine-2-il)ethenyl]phenyl}ethenyl]pyridine and 2-[(Z)-2-{2-[(E)-2-(pyridine-2-il)ethenyl]phenyl}ethenyl]pyridine have been successfully isolated. Newly synthesized derivate was subjected to photochemical reactions at 300 nm and 350 nm to obtain new polycyclic structures via photochemical methodology. Photochemical reaction of 1,2-bis(2-(piridine-2-il)vinyl)benzene leads to dimer product 1,2,3,4-tetra(pyridin-2-yl)cyclobutane (3’). Unidentified intermediated compounds were seen in raw spectra that couldn't be isolated due to their chromatographic instability and subsequent decomposition. Initial compound, as well as photochemical product 3’, has been characterized with modern spectroscopic methods (one-dimensional and two-dimensional NMR, UV/VIS spectroscopy). |
