Strategies to Enhance the Photosensitization: Polymerization and the Donor-Acceptor Even-Odd Effect

Angew Chem Int Ed Engl. 2018 Nov 12;57(46):15189-15193. doi: 10.1002/anie.201810326. Epub 2018 Oct 22.

Abstract

A particular challenge in the design of organic photosensitizers (PSs) with donor-acceptor (D-A) structures is that it is based on trial and error rather than specific rules. Now these challenges are addressed by proposing two efficient strategies to enhance the photosensitization efficiency: polymerization-facilitated photosensitization and the D-A even-odd effect. Conjugated polymers have been found to exhibit a higher 1 O2 generation efficiency than their small molecular counterparts. Furthermore, PSs with A-D-A structures show enhanced photosensitization efficiency over those with D-A-D structures. Theoretical calculations suggest an enhanced intersystem crossing (ISC) efficiency by these strategies. Both in vitro and in vivo experiments demonstrate that the resulting materials can be used as photosensitizers in image-guided photodynamic anticancer therapy. These guidelines are applicable to other polymers and small molecules to lead to the development of new PSs.

Keywords: aggregation-induced emission; even-odd effect; fluorescence; photodynamic therapy; polymerization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line, Tumor
  • HeLa Cells
  • Humans
  • Mice, Inbred BALB C
  • Neoplasms / diagnostic imaging
  • Neoplasms / drug therapy*
  • Neoplasms / metabolism
  • Neoplasms / pathology
  • Optical Imaging
  • Photochemotherapy
  • Photosensitizing Agents / chemistry*
  • Photosensitizing Agents / pharmacokinetics
  • Photosensitizing Agents / pharmacology*
  • Photosensitizing Agents / therapeutic use
  • Polymerization*
  • Polymers / chemistry*
  • Polymers / pharmacokinetics
  • Polymers / pharmacology*
  • Polymers / therapeutic use
  • Singlet Oxygen / metabolism*

Substances

  • Photosensitizing Agents
  • Polymers
  • Singlet Oxygen