Funkcionalizacija pirola u svrhu priprave fluorescentnog indikatora

undergraduate thesis

• Title (english): Preparation of a fluorescent indicator via pyrrole funcionalization
• Author: Barbara Pavlović
• Mentor: Irena Škorić (mentor)
• Mentor: Marija Alešković (komentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Petar Kassal (član povjerenstva)
• Committee member: Marija Alešković (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2020-07-09, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Cilj ovog završnog rada bila je priprava klor supstituiranih
4,4-difluor-4-bor-3a,4a-diaza-s-indacena, BODIPY spojeva koji će kasnije poslužiti kao prekursori u sintezi novih fluorescentnih indikatora, potencijalnih kemosenzora ili obilježavača bioloških makromolekula. Proveden je niz reakcija od kojih je prva reakcija priprava dipirometana Lindseyjevom metodom, počevši od pirola i njegove kondezacije s benzaldehidom uz trifluoroctenu kiselinu kao katalizator. Dobiven je 5-fenildipirometan (5) u vrlo dobrom iskorištenju iz dviju reakcija u kojima su korišteni različiti omjeri pirola i benzaldehida. Dobiveni dipirometan je halogeniran uz N-klorsukcinimid pri dvije različite temperature. Dobiveni dipirometani 1,1'-diklor-5-fenildipirometan (3) i
1-klor-5-fenildipirometan (4) potom su bez izolacije prevedeni u odgovarajuće dipirometene uz 2,3-diklor-5,6-dicijano-1,4-benzokinonon (DDQ) i kompleksirani s borovim trifluoridom kao Lewisovom kiselinom. Preparativnom tankoslojnom kromatografijom izoliran je ciljni spoj
3,5-diklor-4,4-difluor-4-bor-3a,4a-diaza-s-indacen (1). Reakcije su provedene u strogo kontroliranim, inertnim uvjetima uz zaštitu od svjetla, a kao otapala korišteni su suhi diklormetan, toluen i THF. Svi sintetizirani spojevi okarakterizirani su spektroskopskim metodama 1H i 13C NMR.

Abstract (english)

The objective of this final thesis was the preparation of chlorine substituted
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene, BODIPY compounds which will later be utilized as precursors in the synthesis of a new fluorescent indicator, potential chemosensors or biological macromolecule marker. A series of reactions were conducted, the first one being the preparation of dipyrromethane by the Lindsey method, which uses pyrrole and benzaldehyde as starting molecules that undergo condensation with trifluoroacetic acid as catalyst. 5-Phenyldipyrromethane (5) was obtained in a very good reaction yield from two batches of the given reaction, which used different ratios of pyrrole and benzaldehyde. Dipyrromethane was then halogenated using N-chlorosuccinimide at two different temperatures. The acquired 1,1'-dichloro-5-phenyldipyrromethane (3) and
1-chloro-5-phenyldipyrromethane (4) were then, without prior isolation of the compounds, subjected to oxidation into the corresponding dipyrromethene using
2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) followed by complexation with boron trifluoride as a Lewis acid. 3,5-Dichloro-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (1) was isolated by preparative thin layer chromatography. The reactions were conducted in controlled, inert conditions while also being protected from the light. THF, toleuene and dichloromethane were used as solvents. All of the synthesised compounds were characterized using 1H and 13C NMR spectroscopic methods.

• Keywords: elektrofilna aromatska supstitucija; pirol; dipirometan; dipirometen; Lindseyjeva metoda; BODIPY
• Keywords (english): electrophilic aromatic substitution; pyrrole; dipyrromethane; dipyrromethene; Lindsey method; BODIPY
• Language: croatian
• URN:NBN: urn:nbn:hr:149:802476
• Project: Number: 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 programme: Title: Applied Chemistry - Undergraduate 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: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2023-05-08 11:00:38