Aromatski azidi i alkini kao reagensi za sintezu D-Π-A kromofora s 1,2,3-triazolnom poveznicom

undergraduate thesis

• Title (english): Aromatic azides and alkynes as reagents for synthesis of D-Π-A chromophores with 1,2,3-triazole linker
• Author: Magdalena Eškinja
• Mentor: Svjetlana Krištafor (mentor)
• Committee member: Svjetlana Krištafor (predsjednik povjerenstva)
• Committee member: Lidija Furač (član povjerenstva)
• Committee member: Dajana Kučić Grgić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2019-09-20, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

D-π-A sustavi sadržavaju elektron-donorsku (D) i elektron-akceptorsku (A) skupinu koje su povezane konjugiranom organskom poveznicom tzv. π-poveznicom. Često se kao poveznica upotrebljava 1,2,3-triazol koji omogućuje izravnu interakciju donorske i akceptorske skupine prilikom čega dolazi do prijenosa naboja, a ovakvi sustavi mogu se koristiti kao optički kemijski senzori. U ovom radu dan je pregled donorsko-akceptorskih sustava kao kromofora koji sadrže 1,2,3-triazolni prsten u strukturi, te je objašnjen koncept click kemije za sintezu 1,2,3-triazolnih derivata. Cilj rada bila je priprava aromatskih azida i alkina koji bi poslužili kao reagensi za sintezu 1,4-disupstituiranih derivata 1,2,3-triazola baziranih na benztiazolu kao elektron odvlačećoj skupini. Početni spoj 2-aminobenztiazol preveden je u azid nukleofilnom supstitucijom s natrijevim azidom. Provedena je Sonogashira reakcija čiji je cilj bila sinteza 2-etinilbenztiazola iz 2-aminobenztiazola. Dobiveni reagensi podvrgnuti su click reakciji s odgovarajućim alkinom i azidom za pripravu potencijalnih donorsko-akceptorskih sustava s 1,2,3-triazolnom π-poveznicom temeljenih na benztiazolu.

Abstract (english)

D-π-A systems contain electron-donor (D) and electron-acceptor (A) group linked by a conjugated organic linker, so-called π-linker. 1,2,3-triazole is often used as a linker, which allows direct interaction between donor and acceptor group resulting in charge transfer. Such D-π-A systems can be applied in the design of optical chemical sensors. This paper presents an overview of donor-acceptor systems as chromophores containing 1,2,3-triazole ring in their structure, and the concept of click chemistry for synthesis of 1,2,3-triazole derivatives has been explained. The purpose of this work was the preparation of aromatic azides and alkynes, which would serve as reagents for the synthesis of 1,4-disubstituted 1,2,3-triazole derivatives based on benzothiazole as an electron-withdrawing group. The initial 2-aminobenzthiazole compound was converted into corresponding azide by nucleophilic substitution with sodium azide. The Sonogashira reaction as a method for the synthesis of 2-ethynylbenzothiazole from 2-aminobenzothiazole was carried out. The obtained reagents were subjected to click reaction with the corresponding alkyne and azide for the preparation of potential donor-acceptor systems with a 1,2,3-triazole π-linker based on benzothiazole.

• Keywords: click kemija; 1 2 3 triazol; benztiazol; D-π-A sustavi; azidi; alkini
• Keywords (english): click chemistry; 1 2 3-triazole; benzothiazole; D-π-A systems; azides; alkynes
• Language: croatian
• URN:NBN: urn:nbn:hr:149:440415
• 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 13:33:55