Synthesis and In Vitro Antimicrobial Evaluation of Photoactive Multi-Block Chalcone Conjugate Phthalimide and 1,8-Naphthalimide Novolacs.

Periyan Durairaju,Perumberkandigai Adikesavan Vivekanand,Chinnasamy Umarani,Mostafizur Rahaman,Govindasami Periyasami

doi:10.3390/polym13111859

Periyan Durairaju, Perumberkandigai Adikesavan Vivekanand + Show 3 more

Open Access

https://doi.org/10.3390/polym13111859

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Journal: Polymers	Publication Date: Jun 3, 2021
Citations: 8	License type: CC BY 4.0

Affiliation: Thiruvalluvar University, King Saud University

Abstract

Herein we report new multiblock chalcone conjugate phthalimide and naphthalimide functionalized copolymers with a topologically novel architecture synthesis using nucleophilic substitution and polycondensation methodology. The structures of the synthesized novolacs were elucidated on the basis of their spectroscopic analysis including FTIR, 1H NMR, and 13C NMR spectroscopy. Further, the number-average and weight-average molecular weights of the novolac polymers were determined by gel permeation chromatography (GPC). We examined the solubility of the synthesized polymers in various organic solvents including CHCl3, CH3CN, THF, H2O, CH3OH, DMSO, and DMF and found they are insoluble in both methanol and water. The novolac polymers were evaluated for their photophysical properties and microbial activities. The investigation of the antimicrobial activities of these polymers reveals significant antimicrobial activity against the pathogens E. coli, S. aureus, C. albicans, and A. niger.

Highlights

We propose the synthesis and characterization of a new type of highly structured chalcone conjugated fluorescent resins bearing naphthalimide and phthalimide pendants on the novolac backbone
We found the molecular weights of the novalac polymers using gas permutation chromatography (GPC), a reliable and systematic technique
The synthesis of phthalimide analogs 5a–c and 1,8-naphthalimide analogs 9a–d was performed as depicted in Schemes 1 and 2, starting from key materials 1 and 2 and 1 and 6, respectively

Summary

Introduction

Among the various available fluorescent materials in the literature, polymeric compounds containing phthalimides and 1,8-naphthalimide analogs exhibit a wide range of applications [1,2,3]. The structural feature of –CO–N(R)–CO– and the imide ring functionality in phthalimides are responsible for the bioactivity and pharmaceutical properties of the analogs. Due to their hydrophobic and neutral nature, phthalimides can cross biological membranes in vivo [4]. They exhibit antioxidant and anti-inflammatory properties [5,6], have antimicrobial potential [7], and possess anthelmintic activity [8]. Phthalimide polymers are widely used in biomedical and biological fields with a variety of properties including antimalarial, anti-influenza, anticancer, anti-inflammatory, and antifungal activities, apoptotic-inducing properties, and in applications such as protein sensors, n-type organic semiconductors, and electroluminescence [10,11,12,13,14]

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