Synthesis of naphthalene-based push-pull molecules with a heteroaromatic electron acceptor

Šarlah, David (avtor), Juranovič, Amadej (avtor), Kožar, Boris (avtor), Rejc, Luka (avtor), Golobič, Amalija (avtor), Petrič, Andrej (avtor)

Naphthalene derivatives bearing electron-accepting and electron-donating groups at the 2,6-positions belong to the family of D-π-A push-pull dyes. It has been found that these compounds, e.g., 2-(1-(6-((2-(fluoro)ethyl)(methyl)amino)naphthalen-2-yl)ethylidene)malononitrile (FDDNP), show not only interesting optical properties, such as solvatochromism, but they have the potential to label protein aggregates of different compositions formed in the brain of patients suffering from neurodegenerative diseases like Alzheimer’s (AD). In continuation of our research we set our goal to find new FDDNP analogs, which would inherit optical and binding properties but hopefully show better specificity for tau protein aggregates, which are characteristic for neurodegeneration caused by repetitive mild trauma. In this work we report on the synthesis of new FDDNP analogs in which the acceptor group has been formally replaced with an aromatic five- or six-membered heterocycle. The heterocyclic moiety was annealed to the central naphthalene ring either by classical ring closure reactions or by modern transition metal-catalyzed coupling reactions. The chemical characterization, NMR spectra, and UV/vis properties of all new compounds are reported.

• Jezik: Angleški jezik
• Ključne besede: FDDNP analogs, push-pull dyes, heterocyclization, cross-coupling reactions, UV/vis spectroscopy
• Vrsta gradiva: Članek v reviji
• Tipologija: 1.01 - Izvirni znanstveni članek
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Status publikacije: Objavljeno
• Različica publikacije: Objavljena publikacija
• Leto izida: 2016
• Št. strani: 16 str.
• Številčenje: Vol. 21, iss. 3, art. 267
• PID: 20.500.12556/RUL-130313
• UDK: 547.65.057
• ISSN pri članku: 1420-3049
• DOI: 10.3390/molecules21030267
• COBISS.SI-ID: 1536799939
• Datum objave v RUL: 13.09.2021

Gradivo je del revije

• Naslov: Molecules
• Skrajšan naslov: Molecules
• Založnik: MDPI
• ISSN: 1420-3049
• COBISS.SI-ID: 18462981

Licence

• Licenca: CC BY 4.0, Creative Commons Priznanje avtorstva 4.0 Mednarodna
• Povezava: http://creativecommons.org/licenses/by/4.0/deed.sl
• Opis: To je standardna licenca Creative Commons, ki daje uporabnikom največ možnosti za nadaljnjo uporabo dela, pri čemer morajo navesti avtorja.
• Začetek licenciranja: 02.03.2016

Sekundarni jezik

• Jezik: Slovenski jezik
• Ključne besede: organska kemija, analogi FDDNP, push-pull barvila, heterociklizacije, cross-coupling reakcije, UV/vis spektroskopija

Projekti

• Financer: ARRS - Agencija za raziskovalno dejavnost Republike Slovenije
• Številka projekta: P1-0230
• Naslov: Organska kemija: sinteza, struktura in aplikacija