Synthesis and investigation on optical and electrochemical properties of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridines

Najeh Tka; Mohamed Adnene Hadj Ayed; Mourad Ben Braiek; Mahjoub Jabli; Peter Langer

doi:10.3762/bjoc.17.162

Synthesis and investigation on optical and electrochemical properties of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridines

Beilstein J Org Chem. 2021 Sep 20:17:2450-2461. doi: 10.3762/bjoc.17.162. eCollection 2021.

Authors

Najeh Tka^{1

2}, Mohamed Adnene Hadj Ayed¹, Mourad Ben Braiek¹, Mahjoub Jabli³, Peter Langer^{2

4}

Affiliations

¹ Laboratory of Asymmetric Synthesis and Molecular Engineering for Organic Electronic Materials (LR18ES19), Monastir University, Faculty of Sciences of Monastir, 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 Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany.

Abstract

A facile synthesis of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridine derivatives is reported which is based on POCl₃-mediated cyclodehydration followed by double Suzuki-Miyaura cross-coupling. The absorption and fluorescence properties of the obtained products were investigated and their HOMO/LUMO energy levels were estimated by cyclic voltammetry measurements. Besides, density functional theory calculations were carried out for further exploration of their electronic properties.

Keywords: catalysis; cross-coupling; cyclization; fluorescence; palladium.

Grants and funding

This study was supported by the Ministry of Higher Education and Scientific Research-Tunisia. Financial support from the DAAD (scholarship for N. T.) is gratefully acknowledged.