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Molecules 2016, 21(3), 267; doi:10.3390/molecules21030267

Synthesis of Naphthalene-Based Push-Pull Molecules with a Heteroaromatic Electron Acceptor

1
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, 1000 Ljubljana, Slovenia
2
EN-FIST Centre of Excellence, Trg Osvobodilne fronte 13, SI-1000 Ljubljana, Slovenia
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editor: Wim Dehaen
Received: 4 January 2016 / Revised: 18 February 2016 / Accepted: 22 February 2016 / Published: 2 March 2016
(This article belongs to the Collection Heterocyclic Compounds)
View Full-Text   |   Download PDF [1573 KB, uploaded 2 March 2016]   |  

Abstract

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. View Full-Text
Keywords: FDDNP analogs; push-pull dyes; heterocyclization; cross-coupling reactions; UV/vis spectroscopy FDDNP analogs; push-pull dyes; heterocyclization; cross-coupling reactions; UV/vis spectroscopy
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Šarlah, D.; Juranovič, A.; Kožar, B.; Rejc, L.; Golobič, A.; Petrič, A. Synthesis of Naphthalene-Based Push-Pull Molecules with a Heteroaromatic Electron Acceptor. Molecules 2016, 21, 267.

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