The Effect of Branching on the One- and Two-Photon Absorption, Cell Viability, and Localization of Cationic Triarylborane Chromophores with Dipolar versus Octupolar Charge Distributions for Cellular Imaging

Chemistry. 2019 Oct 11;25(57):13164-13175. doi: 10.1002/chem.201902461. Epub 2019 Sep 17.

Abstract

Two different chromophores, namely a dipolar and an octupolar system, were prepared and their linear and nonlinear optical properties as well as their bioimaging capabilities were compared. Both contain triphenylamine as the donor and a triarylborane as the acceptor, the latter modified with cationic trimethylammonio groups to provide solubility in aqueous media. The octupolar system exhibits a much higher two-photon brightness, and also better cell viability and enhanced selectivity for lysosomes compared with the dipolar chromophore. Furthermore, both dyes were applied in two-photon excited fluorescence (TPEF) live-cell imaging.

Keywords: boranes; cell imaging; fluorescence; lysosome; two-photon excited fluorescence.

MeSH terms

  • Aniline Compounds / chemistry*
  • Cations / chemistry*
  • Cell Survival*
  • Molecular Structure
  • Photons
  • Solubility
  • Spectrometry, Fluorescence

Substances

  • Aniline Compounds
  • Cations