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

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

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
Article number267
JournalMolecules
Volume21
Issue number3
DOIs
StatePublished - Mar 2016
Externally publishedYes

Keywords

  • Cross-coupling reactions
  • FDDNP analogs
  • Heterocyclization
  • Push-pull dyes
  • UV/vis spectroscopy

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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