| Summary: | 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, <sup>1</sup>H NMR, and <sup>13</sup>C 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 CHCl<sub>3</sub>, CH<sub>3</sub>CN, THF, H<sub>2</sub>O, CH<sub>3</sub>OH, 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 <i>E. coli</i>, <i>S. aureus</i>, <i>C. albicans</i>, and <i>A. niger</i>.
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