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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. 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. |
