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

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

doi:10.3762/bjoc.17.162

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.

Highlights

Introduction πConjugated organic molecules are finding use in numerous areas ranging from organic electronics [1,2,3,4,5], ions sensing [6,7], and solar cell development [8,9,10]
In continuation to our previous work and as a part of our interest in new organic materials [58,59,60], we report the synthesis of hitherto unknown 2,4-diaryl-9chloro-5,6,7,8-tetrahydroacridine derivatives and their optical and electrochemical properties investigation by the use of UV–vis and emission spectroscopy, cyclic voltammetry (CV) measurements as well as density functional theory (DFT) calculations
We developed a convenient synthesis of novel 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridines starting from commercially available anthranilic acid

Summary

Introduction

Conjugated organic molecules are finding use in numerous areas ranging from organic electronics [1,2,3,4,5], ions sensing [6,7], and solar cell development [8,9,10] Within this background, acridines represent an interesting class of heteroaromatic π-conjugated compounds [11,12,13,14] which show great perspectives in medicinal chemistry [15,16,17,18,19,20,21,22,23], dye industries [24,25,26], and metal chemo sensing [27,28,29].

Methods

Results

Conclusion