N,N-ditriazolil-heteroaril supstituirani derivati anilina u koordiniranju iona metala

undergraduate thesis

• Title (english): N,N-ditriazolyl-heteroaryl substituted aniline derivatives in metal ion coordination
• Author: Karla Hmelina
• Mentor: Svjetlana Krištafor (mentor)
• Committee member: Svjetlana Krištafor (predsjednik povjerenstva)
• Committee member: Lidija Furač (član povjerenstva)
• Committee member: Marijana Hranjec (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2019-09-16, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Cilj rada je click reakcijama pripraviti nove N,N-disupstituirane derivate anilina i odabranih heteroaromatskih jezgri međusobno povezanih 1,2,3-triazolnim prstenom. Click reakcijom pripravljeni 1,2,3-triazolni prsten je zbog svog dipolnog karaktera i prisutnosti dušikovih atoma sa slobodnim elektronskim parovima česta struktura u koordiniranju metalnih kationa. Sinteza željenih derivata je provedena u tri koraka, gdje su u prvom koraku, pripravljeni N-mono- i N,N-dipropargilirani derivati anilina. U drugom koraku su iz anilina,
7-amino-4-metilkumarina i 2-aminobenztiazola pripremljeni odgovarajući aromatski azidi reakcijom nukleofilne supstitucije s natrijevim azidom u prisutnosti natrijeva nitrita. Konačni spojevi pripremljeni su u trećem koraku click reakcijama između alkina i odgovarajućih aromatskih azida, a strukture dobivenih spojeva potvrđene su 1H i 13C NMR spektroskopijom. Nadalje, provjerena je potencijalna primjena sintetiziranog
N,N-bis((1-fenil-1H-1,2,3-triazol-4-il)metil)anilina (5) kao kemosenzora ispitivanjem spektralnih karakteristika u prisutnosti metalnih iona UV-vidljivom spektroskopijom. Za ispitivanje utjecaja metalnih kationa, u pripravljenu otopinu spoja 5 dodavan je određeni alikvot otopine metalnih kationa u omjeru spoj: metalni ion = 1:1 i 1:5.

Abstract (english)

The aim of this work was to prepare the new N,N-disubstituted aniline and heteroaryl derivatives linked by a 1,2,3-triazole ring using click reactions. The 1,2,3-triazole ring generated by the click reaction is a common motif in metal ion coordination chemistry, due to its dipole character and the presence of nitrogen atoms with free electron pairs. The synthesis was carried out in three steps. In the first step N-mono- and N,N-dipropargylated aniline derivatives were prepared. In the second step, the corresponding aromatic azides were prepared from aniline, 7-amino-4-methylcoumarin and 2-aminobenzthiazole by nucleophilic substitution with sodium azide in the presence of sodium nitrite. The target compounds were prepared by click reactions of alkynes and corresponding azides. The structures of the newly prepared compounds were confirmed by 1H and 13C NMR spectroscopy. Furthermore, the potential application of
N,N-bis((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)aniline (5) as chemosensor for metal ions was evaluated by UV–Vis spectroscopy. To test the influence of metal cations on spectral properties of compound 5, absorption spectra of 5 in presence of metal ions (1.0 and 5.0 equivalents) were recorded.

• Keywords: click kemija; kemosenzor; 1 2 3-triazol; koordiniranje metalnih iona; spektroskopija; derivati anilina
• Keywords (english): click chemistry; chemosensor; 1 2 3-triazole; metal ion coordination; spectroscopy; aniline derivatives
• Language: croatian
• URN:NBN: urn:nbn:hr:149:802492
• 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: 2023-05-23 12:33:11