Sinteza i spektroskopska karakterizacija imino-kumarina N-supstituiranih benzimidazola kao potencijalnog senzora za metalne katione i pH u otopinama

undergraduate thesis

• Title (english): Synthesis and spectroscopic characterization of N-substituted benzimidazole imino-coumarine as potential sensor for metal cations and pH in solution
• Author: Kristina Crnjac
• Mentor: Marijana Hranjec (mentor)
• Committee member: Marijana Hranjec (predsjednik povjerenstva)
• Committee member: Jasna Prlić Kardum (član povjerenstva)
• Committee member: Ema Horak (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2019-09-06, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je sinteza i spektroskopska karakterizacija N-benzimidazolil supstituranih derivata iminokumarina. Ciljani spojevi su priređeni klasičnim metodama organske sinteze te nekataliziranom aminacijom potpomognutom mikrovalnim zračenjem. Derivati 4-nitrobenzonitrila 3 i 4 priređeni su reakcijom nukleofilne aromatske supstitucije potpomognute mikrovalovima iz 3-klor-4-benzonitrila 1. Reakcijom redukcije iz spojeva 3 i 4 priređeni su amino supstituirani derivati 6 i 7. Kondenzacijom spojeva 6, 7 i 8 s 2-cijanoacetamidom dobiveni su derivati 2-cijanometilbenzimidazola 9, 10 i 11. Ciljani derivati 7-N,N-dietilamino-2-imino-3-benzimidazolilkromena 13, 14 i 15 priređeni su reakcijom aldolne kondenzacije iz pripravljenih spojeva 9, 10 i 11 i 4-N,N-dietilamino-2-hidroksibenzaldehida 12. Stuktura svih priređenih spojeva potvrđena je korištenjem 1H i 13C NMR spektroskopije te dodatno i masenom spektrometrijom. Ciljani spojevi 13, 14 i 15 su okarakterizirani UV/Vid i fluorimetrijskom spektroskopijom u nekoliko otapala različite polarnosti. Kako bi se ispitala njihova moguća primjena kao senzora za detekciju pH i metalnih kationa, provedene su i UV/Vid titracije otopina spojeva s otopinama metalnih soli i u puferima različitog pH.

Abstract (english)

The aim of this study was the synthesis and spectroscopic characterization of N-benzimidazole substitued iminocoumarines. Targeted compounds were prepared by classical reactions of organic chemistry and uncalatyzed microwave assisted amination. Derivates of 4-nitrobenzonitrile 3 and 4 were prepared by microwave assisted reaction of nucleophilic aromatic substitution from 3-chloro-4-nitrobenzonitrile 1. Within the reduction of compounds 3 and 4 amino substituted derivates 6 and 7 obtained. Derivates of 2-cyanomethylbenzimidazoles 9, 10 and 11 were prepared using condensation of compounds 6, 7 and 8 with 2-cyanoacetamide. Targeted derivates of 7-N-N-diethylamino-2-imino-3-benzimidazolyl-chromen 13, 14 and 15 were prepared by aldol condensation from compounds 9, 10 and 11 and 4-N,N-dietylamino-2-hydroxybenzaldehyde 12. The structures of all synthesized compounds were confirmed by means of 1H and 13C spectroscopy and additionally with mass spectrometry. Targeted compounds 13, 14 and 15 were characterized by UV/Vis and fluorimetric spectroscopy in several organic solvents having different polarity. In order to explore the possible application of compounds 13, 14 and 15 as sensors for detection pH and metal cations, UV/Vis titration of aqueous compounds solutions with aqueous solutions of metal salts and with buffer solutions with different pH were performed.

• Keywords: iminokumarin; benzimidazol; UV/Vid; fluorimetrijska i NMR spektroskopija; kemijski senzor; pH senzor
• Keywords (english): iminocoumarine; benzimidazole; UV/Vis; fluorimetric and NMR spectroscopy; chemical sensors; pH sensors
• Language: croatian
• URN:NBN: urn:nbn:hr:149:757240
• Project: Number: IP-2018-01-4379; Title: Istraživanje antioksidativnog djelovanja benzazolskog skeleta u dizajnu novih antitumorskih agensa; Acronym: AntioxPot; Leader: Marijana Hranjec; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• Project: Number: IP-2014-09-3386; Title: Dizajn i sinteza novih dušikovih heterocikličkih fluorofora i fluorescentnih nanomaterijala kao kemijskih senzora za pH i metalne ione; Title: Design and Synthesis of Novel Nitrogen-Containing Heterocyclic Fluorophores and Fluorescent Nanomaterials for pH and Metal-Ion Sensing; Acronym: iNFiNiTE–SENS; Leader: Robert Vianello; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• Study programme: Title: Chemical Engineering - Undergraduate study; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva (sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Access restricted to students and staff of home institution
• Created on: 2023-02-14 08:50:56