5,12-Dihydroindolo[3,2-a]Carbazole Derivatives-Based Water Soluble Photoinitiators for 3D Antibacterial Hydrogels Preparation

Small. 2023 Dec;19(50):e2300772. doi: 10.1002/smll.202300772. Epub 2023 Mar 3.

Abstract

Indolo[3,2-a]carbazole alkaloids have drawn a growing interest in recent years owing to their potential electrical and optical properties. With 5,12-dihydroindolo[3,2-a]carbazole serving as the scaffold, two novel carbazole derivatives are synthesized in this study. Both compounds are extremely soluble in water, with solubility surpassing 7% in weight. Intriguingly, the introduction of aromatic substituents contributed to drastically reduce the π-stacking ability of carbazole derivatives, while the presence of the sulfonic acid groups enables the resulting carbazoles remarkably soluble in water, allowing them to be used as especially efficient water-soluble PIs in conjunction with co-initiators, i.e., triethanolamine and the iodonium salt, respectively, employed as electron donor and acceptor. Surprisingly, multi-component photoinitiating systems based on these synthesized carbazole derivatives could be used for the in situ preparation of hydrogels containing silver nanoparticles via laser write procedure with a light emitting diode (LED)@405 nm as light source, and the produced hydrogels display antibacterial activity against Escherichia coli.

Keywords: 3D printing; antibacterial hydrogel; carbazole; metal nanoparticles; photopolymerization; water-soluble photoinitiating systems.

MeSH terms

  • Carbazoles
  • Hydrogels*
  • Metal Nanoparticles*
  • Silver
  • Water

Substances

  • carbazole
  • Hydrogels
  • Water
  • Silver
  • Carbazoles