Synthesis, characterization, and antibacterial activity of azodyes incorporated acridine chromophore and their applications in polyester printing

Khalid Hassan,Ghada M Elhaddad,Asmaa B Sallam,Ibrahim El Sayed,El-Khabiry Shaban

doi:10.5267/j.ccl.2021.9.002

Abstract

A series of azo dyes incorporated acridine chromophore labelled as 8 (a-d), 10 (a, b), 12 and 14 were prepared in very good yields starting from 9-chloroacridine 1 followed by amination, diazotization and coupling either with rhodanine analogues 6 (a, b) or other coupling partners 9 (a, b), 11 and 13. FT-IR, 1H NMR, and mass spectroscopic analysis were used to establish the structures of the produced azo dispersed dyes. Moreover, the synthesized azo dyes were used to prepare pastes that were used to print polyester fabric using classic silk-screen printing techniques. The dyes were tested for color strength and fastness properties, and they showed good fastness resistance to washing, rubbing, and perspiration, as well as fastness to sublimation and light. The dyes were further screened for their in vitro antibacterial activity against both Gram (+) and Gram (-) bacterial species. Most of them showed promising activities against these tested organisms.

Highlights

Due to their unique structures, synthetic azo dyes are considered as one of the main class of dyes used in different application such as anticancer,1-4 antibacterial,1-3 antioxidant,2,5 antitumor,6 and anti-inflammatory.7 The dyeing of different textile fabrics by active biological azo structures are the most widely used class of dyes.8 Mono azo dyes based on different heterocyclic amine such as acridine moiety have been developed and the product of this type of dyes has higher strength and becomes brighter than those obtained from aniline
The synthesis of the target amino acridines benzene-1,3-diamine 3a or benzene-1,4diamine 3b was obtained in very good yields according to the protocol shown in Scheme 1
The Fourier transform infrared (FT-IR) for 6b shows significant vibration bands at 3228, 3050, 2924, 1680, 1588 and 1205 cm-1 relating to the presence of (OH), (=CH), (-CH2-), (-C=C-), (C=O) and (C=S) groups, respectively

Summary

Introduction

Due to their unique structures, synthetic azo dyes are considered as one of the main class of dyes used in different application such as anticancer, antibacterial, antioxidant, antitumor, and anti-inflammatory. The dyeing of different textile fabrics by active biological azo structures are the most widely used class of dyes. Mono azo dyes based on different heterocyclic amine such as acridine moiety have been developed and the product of this type of dyes has higher strength and becomes brighter than those obtained from aniline. The dyeing of different textile fabrics by active biological azo structures are the most widely used class of dyes.. Acridines bearing rhodanine moiety and azo chromophore are important scaffold in broad spectrum activities in medicinal chemistry due to their diverse biological properties such as antimalarial, antibacterial, anticancer and DNA-intercalating agents.. The utilizing of Nheterocyclic such as acridine azo compounds allows them to bind with polyester textile fabrics by printing method is a hot point in an antibacterial test. These structures are an advantage by the presence of planner tricyclic fused aromatic system, and one or two flexible substituted pharmacophoric groups at different core position on the acridine skeleton.

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