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master's thesis
Sinteza i fotokemija BODIPY spojeva s fenolnim supstituentom na borovom atomu
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2022. urn:nbn:hr:149:273636
Bogomolec, Marko
University of Zagreb
Faculty of Chemical Engineering and Technology

Institutional repository: Repository of Faculty of Chemical Engineering and Technology University of Zagreb

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Bogomolec, M. (2022). Sinteza i fotokemija BODIPY spojeva s fenolnim supstituentom na borovom atomu (Master's thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:273636

Bogomolec, Marko. "Sinteza i fotokemija BODIPY spojeva s fenolnim supstituentom na borovom atomu." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2022. https://urn.nsk.hr/urn:nbn:hr:149:273636

Bogomolec, Marko. "Sinteza i fotokemija BODIPY spojeva s fenolnim supstituentom na borovom atomu." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2022. https://urn.nsk.hr/urn:nbn:hr:149:273636

Bogomolec, M. (2022). 'Sinteza i fotokemija BODIPY spojeva s fenolnim supstituentom na borovom atomu', Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 05 January 2025, https://urn.nsk.hr/urn:nbn:hr:149:273636

Bogomolec M. Sinteza i fotokemija BODIPY spojeva s fenolnim supstituentom na borovom atomu [Master's thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2022 [cited 2025 January 05] Available at: https://urn.nsk.hr/urn:nbn:hr:149:273636

M. Bogomolec, "Sinteza i fotokemija BODIPY spojeva s fenolnim supstituentom na borovom atomu", Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2022. Available at: https://urn.nsk.hr/urn:nbn:hr:149:273636

Metadata
TitleSinteza i fotokemija BODIPY spojeva s fenolnim supstituentom na borovom atomu
Title (english)Synthesis and photochemistry of BODIPY compounds substituted at the boron atom
AuthorMarko Bogomolec
MentorIrena Škorić (mentor)
MentorNikola Basarić (komentor)
Committee memberIrena Škorić (predsjednik povjerenstva)
Committee memberTatjana Gazivoda Kraljević (član povjerenstva)
Committee memberAnte Jukić (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2022-09-28, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
U ovom radu opisana je sinteza i fotokemija novih derivata BODIPY spojeva 2–7 koji su supstituirani na atomu bora s jednim ili dva fenolna supstituenta. Derivati 6 i 7, imaju jedan, odnosno dva para-acetoksimetilfenolna supstituenta. Hipoteza istraživanja bila je da će osvjetljavanjem spojeva 2–7 vidljivim svjetlom doći do heterolize B–O veze i eliminacije fenolata iz kojih bi u slučaju spojeva 6 i 7 naknadnom eliminacijom acetata nastali kinon-metidi (QM). Fotokemijsko nastajanje QM zanimljivo je radi njihove antiproliferativne aktivnosti. Sintetizirani spojevi okarakterizirani su spektroskopijom 1H i 13C NMR te spektrometrijom masa. Spektroskopska i fotofizička svojstva spojeva 1–7 ispitana su UV-Vis spektroskopijom i stacionarnom i vremenski razlučenom fluorescencijskom spektroskopijom. Fotokemijska reaktivnost ispitana je osvjetljavanjem otopina spojeva 2–7 u metanolu, a produkti metanolize su izolirani i okarakterizirani spektroskopskim metodama. Izolirani produkti ukazuju da osvjetljavanjem dolazi do heterolize B–O veza. Međutim, nije dokazano nastajanje QM. Fotofizička istraživanja dovedena su u vezu s fotokemijskim ispitivanjima kako bi se utvrdilo ovise li kvantni prinosi fluorescencije i eliminacije fenolnih skupina o fotoinduciranom prijenosu elektrona između fenoksi-supstituenta i BODIPY dijelova molekule.
Abstract (english)
This thesis features the synthesis and photochemistry of new BODIPY derivatives 2–7, which are substituted at the boron atom with one or two phenolic substituents. Derivatives 6 and 7, bear one or two para-acetoxymethylphenol substituents, respectively. The hypothesis of the investigation was that the irradiation of 2-7 by visible light would lead to a heterolysis of the B–O bond and elimination of phenolates, which in the case of 6 and 7 would afford quinone methides (QMs) by subsequent elimination of acetate. Photochemical formation of QMs is interesting owing to their antiproliferative activity. The synthesized compounds were characterized by 1H and 13C NMR spectroscopy and high resolution mass spectrometry. Spectroscopic and photophysical properties of 1-7 were investigated by UV-Vis spectroscopy and stationary and time-resolved fluorescence spectroscopy. The photochemical reactivity was probed by performing irradiations of 2-7 in methanolic solutions whereupon methanolysis products were isolated and characterized by spectroscopic methods. Isolated products indicate that the irradiation leads to the heterolysis of the B-O bonds. However, formation of QMs has not been proved. The photophysical investigation was put in connection with the irradiation studies, probing if the quantum yields of fluorescence and elimination of phenolic groups depend on photoinduced electron transfer between phenoxy substituents and BODIPY.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:273636
ProjectNumber: IP-2019-04-8008
Title: Fotokemija: Reakcijski mehanizmi i primjene u organskoj sintezi i biologiji
Title: Photochemistry: Reaction Mechanisms and Applications in Organic Synthesis and Biology
Acronym: PhotoApp
Leader: Nikola Basarić
Jurisdiction: Croatia
Funder: HRZZ
Funding stream: IP
Study programmeTitle: Applied Chemistry - Graduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry
Course: Applied organic chemistry
Study programme type: university
Study level: graduate
Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
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Created on2023-03-28 09:02:32