2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

Najeh Tka; Mohamed Adnene Hadj Ayed; Mourad Ben Braiek; Mahjoub Jabli; Noureddine Chaaben; Kamel Alimi; Stefan Jopp; Peter Langer

doi:10.3762/bjoc.17.115

2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

Beilstein J Org Chem. 2021 Jul 16:17:1629-1640. doi: 10.3762/bjoc.17.115. eCollection 2021.

Authors

Najeh Tka^{1

2}, Mohamed Adnene Hadj Ayed¹, Mourad Ben Braiek¹, Mahjoub Jabli³, Noureddine Chaaben⁴, Kamel Alimi¹, Stefan Jopp², Peter Langer^{2

5}

Affiliations

¹ Asymmetric Synthesis and Molecular Engineering Laboratory for Organic Electronic Materials, Faculty of sciences of Monastir, Monastir university, Environment street, 5019 Monastir, Tunisia.
² Universität Rostock, Institut für Chemie, Albert-Einstein-Str. 3a, 18059 Rostock, Germany.
³ Department of Chemistry, College of Science Al-zulfi, Majmaah University, Al-Majmaah, 11952, Saudi Arabia.
⁴ Université de Monastir, Faculté des Sciences, Unité de recherche sur les Hétéro-Epitaxies et Applications (URHEA), 5000 Monastir, Tunisia.
⁵ Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany.

Abstract

Acridine derivatives have attracted considerable interest in numerous areas owing to their attractive physical and chemical properties. Herein, starting from readily available anthranilic acid, an efficient synthesis of 2,4-bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridine derivatives was accomplished via a one-pot double Sonogashira cross-coupling method. The UV-visible absorption and emission properties of the synthesized molecules have been examined. Additionally, theoretical studies based on density functional theory (DFT/B3LYP/6-31G(d)) were carried out.

Keywords: alkynes; catalysis; cross-coupling; heterocycles; palladium.

Grants and funding

Financial support from the Deutscher Akademischer Austausch Dienst (DAAD) (scholarship for Najeh TKA) is gratefully acknowledged.