Aggregation-Dependent Photoreactive Hemicyanine Assembly as a Photobactericide

ACS Appl Mater Interfaces. 2020 May 20;12(20):22552-22559. doi: 10.1021/acsami.0c03894. Epub 2020 May 8.

Abstract

Organic materials that show substantial reactivity under visible light have received considerable attention due to their wide applications in chemical and biological systems. Hemicyanine pigments possess a strong intramolecular donor-acceptor structure and thereby display intense absorption in the visible spectral region. However, most excitons are consumed via the twisted intramolecular charge-transfer (TICT) process, making hemicyanines generally inert to light. Herein, we describe the development of an amphiphilic hemicyanine dye whose aggregation could be easily regulated using salt or counterions. More importantly, its intrinsic photoreactivity was successfully induced by steric restriction and cofacial arrangement within the H-aggregate, thus creating an effective photobactericide. This strategy could be extended to the development of photocatalysts for photosynthesis and a photosensitizer for photodynamic therapy.

Keywords: H-aggregate; TICT; photobactericide; photoreactivity; supramolecular self-assembly.

MeSH terms

  • Aniline Compounds / pharmacology*
  • Aniline Compounds / radiation effects
  • Anti-Bacterial Agents / pharmacology*
  • Anti-Bacterial Agents / radiation effects
  • Coloring Agents / pharmacology*
  • Coloring Agents / radiation effects
  • Escherichia coli / drug effects
  • Hydroxyl Radical / metabolism
  • Light
  • Microbial Sensitivity Tests
  • Stilbenes / pharmacology*
  • Stilbenes / radiation effects
  • Surface-Active Agents / pharmacology
  • Surface-Active Agents / radiation effects

Substances

  • Aniline Compounds
  • Anti-Bacterial Agents
  • Coloring Agents
  • Stilbenes
  • Surface-Active Agents
  • Hydroxyl Radical