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master's thesis
Fluorescencija čvrstog stanja heteroaromatskih kromofora u funkcionalnim materijalima
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. urn:nbn:hr:149:093227
Šimanović, Aleksandra
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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Šimanović, A. (2018). Fluorescencija čvrstog stanja heteroaromatskih kromofora u funkcionalnim materijalima (Master's thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:093227

Šimanović, Aleksandra. "Fluorescencija čvrstog stanja heteroaromatskih kromofora u funkcionalnim materijalima." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. https://urn.nsk.hr/urn:nbn:hr:149:093227

Šimanović, Aleksandra. "Fluorescencija čvrstog stanja heteroaromatskih kromofora u funkcionalnim materijalima." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. https://urn.nsk.hr/urn:nbn:hr:149:093227

Šimanović, A. (2018). 'Fluorescencija čvrstog stanja heteroaromatskih kromofora u funkcionalnim materijalima', Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 04 November 2024, https://urn.nsk.hr/urn:nbn:hr:149:093227

Šimanović A. Fluorescencija čvrstog stanja heteroaromatskih kromofora u funkcionalnim materijalima [Master's thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2018 [cited 2024 November 04] Available at: https://urn.nsk.hr/urn:nbn:hr:149:093227

A. Šimanović, "Fluorescencija čvrstog stanja heteroaromatskih kromofora u funkcionalnim materijalima", Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2018. Available at: https://urn.nsk.hr/urn:nbn:hr:149:093227

Metadata
TitleFluorescencija čvrstog stanja heteroaromatskih kromofora u funkcionalnim materijalima
Title (english)Solid-state fluorescence of heteroaromatic chromophores for use in functional materials
AuthorAleksandra Šimanović
MentorIvana Steinberg (mentor)
Committee memberIvana Steinberg (predsjednik povjerenstva)
Committee memberNataša Perin (član povjerenstva)
Committee memberEma Horak (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2018-07-04, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Applied Chemistry
Abstract
U ovom radu je karakterizirano pet derivata benzimidazola s ciljem razvoja novih funkcionalnih materijala: 2-[(4-N,N-dimetilamino)benz-2-ilidenamino]-5(6)-cijanobenzimidazol (1), 2-[(4-N,N-dimetilamino)benz-2-ilidenamino]-5(6)-nitrobenzimidazol (2), 2-[(4-N,N-dietilamino-2-hidroksi)benz-2-ilidenamino]-5(6)-cijanobenzimidazol (3), 2-[(4-N,N-dietilamino-2-hidroksi)benz-2-ilidenamino]-5(6)-nitrobenzimidazol (4) i E-2-(2-benzimidazolil)-3-(4-N,N-dimetilaminofenil)akrilonitril (5). Spojevi su dizajnirani kao D-π-A kromofori s elektron donorskim N,N-dimetil ili N,N-dietil amino skupinama i jakim elektron akceptorskim skupinama -NO2 ili -CN. Fotofizička svojstva spojeva 1-5 ispitana su UV-vidljivom apsorpcijskom i fluorescencijskom spektroskopijom u različitim otapalima, prilikom čega je uočeno stvaranje nanoagregata u vodi i stvaranje novog fluorescencijskog maskimuma pri višim valnim duljinama. Navedena pojava se može opisati kao emisija izazvana agregacijom (engl. Aggregation induced emission, AIE) te upravo ona pruža brojne potencijalne primjene. Fluorofori u čvrstom stanju (engl. solid-state fluorophores) temeljeni na AIE su jedan od široko primjenjivanih primjera funkcionalnih materijala. Iako su vrlo slabo fluorescentni u otopini, spojevi 1-5 pokazuju intenzivnu fluorescenciju u čvrstom stanju. Spektrofotometrijskim metodama je karakterizirana fluorescencija 1-5 u čvrstom stanju te je ispitan utjecaj vanjskih čimbenika na emisiju čvrstog stanja. Emisija spojeva 1-5 uočava se u širokom dijelu elektromagnetskog spektra te golim okom uočavamo fluorescenciju od žute do crvene boje. Crvena emisija spoja 4 je osobito atraktivna jer su crveni fluorofori u čvrstom stanju vrlo rijetki. Većina spojeva pokazuje djelomičnu promjenu fluorescencijskih karakteristika prilikom utjecaja vanjske mehaničke sile. Najizraženija promjena u fluorescencijskim karakteristikama se uočava za spoj 4 (Δλ = 36 nm) te ga možemo okarakterizirati kao reverzibilni mehanokromatski materijal. Spoj 4 je također pokazao najveću osjetljivost na mikrookolinu (atmosferu zasićenu parama organskih otapala) prilikom čega se uočava pad intenziteta fluorescencije s porastom polarnosti otapala.
Abstract (english)
In this work five benzimidazole derivatives were characterised to develop novel functional materials: 2-[(4-N,N-dimethylamino)benz-2-ylideneamino]-5(6)-cyanobenzimidazole (1), 2-[(4-N,N-dimethylamino)benz-2-ylideneamino]-5(6)-nitrobenzimidazole (2), 2-[(4-N,N-diethylamino-2-hydroxy)benz-2-ylideneamino]-5(6)-cyanobenzimidazole (3), 2-[(4-N,N-diethyamino-2-hydroxy)benz-2-ylideneamino]-5(6)-nitrobenzimidazole and E-2-(2-Benzimidazolyl)-3-(4-N,N-dimethylaminophenyl)acrylonitrile (5). Compounds are designed as D-π-A chromophores with electron-donating N,N-dimethyl or N,N-diethyl amino group and strong electron-withdrawing -NO2 and –CN groups. The photophysical properties of compounds 1-5 were investigated by UV-visible absorption and fluorescence spectroscopy in various solvents; the formation of nanoaggregates in water and the creation of a new emission maximum at higher wavelengths was observed. This phenomenon can be described as aggregation induced emission (AIE) and it provides numerous potential applications. Solid-state fluorophores based on AIE are examples of widely used functional materials. Although poorly fluorescent in solution, compounds 1-5 show intense fluorescence in solid-state. Fluorescence of compounds 1-5 was characterised using spectrophotometric methods and the influence of external factors on solid-state was studied. The emission of compounds 1-5 is observed in a wide part of the electromagnetic spectrum and fluorescence from yellow to red is observed by naked eye. The red emission of compound 4 is particularly attractive because the red fluorophores in solid-state are very rare. Most of the compounds show a partial change in the emission characteristics when the external mechanical force is applied. The biggest change in emission characteristics is observed for compound 4 (Δλ = 36 nm) and it can be characterised as a reversible mechanochromic material. Compound 4 also exhibited the highest sensitivity to the microenvironment (a saturated atmosphere of organic solvents) showing a decrease in the fluorescence intensity with the increase of solvent polarity.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:093227
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 on2020-05-08 09:50:38