20.500.12556/RUL-130313 Synthesis of naphthalene-based push-pull molecules with a heteroaromatic electron acceptor 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. FDDNP analogs push-pull dyes heterocyclization cross-coupling reactions UV/vis spectroscopy organska kemija analogi FDDNP push-pull barvila heterociklizacije cross-coupling reakcije UV/vis spektroskopija true false true Angleški jezik Slovenski jezik Članek v reviji 2021-09-13 14:18:40 2021-09-13 14:18:41 2022-09-09 04:15:50 0000-00-00 00:00:00 2016 0 0 16 str. iss. 3, art. 267 Vol. 21 2016 0000-00-00 Zaloznikova Objavljeno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 547.65.057 1420-3049 10.3390/molecules21030267 1536799939 RAZ_Sarlah_David_2016.pdf RAZ_Sarlah_David_2016.pdf 1 47D3DA0D7B038C0C08CE2E7FD14BF628 ec48b470fb5aab60429e42e01843c8672be36d2a812356e5fad94b813f776571 0531ed00-148e-11ec-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=147401 http://www.mdpi.com/1420-3049/21/3/267 1 7ab1d4dd-148c-11ec-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=147396 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0