Self-Assembly of Electron Donor-Acceptor-Based Carbazole Derivatives: Novel Fluorescent Organic Nanoprobes for Both One- and Two-Photon Cellular Imaging

ACS Appl Mater Interfaces. 2016 May 11;8(18):11355-65. doi: 10.1021/acsami.6b03259. Epub 2016 Apr 29.

Abstract

In this study, we report fluorescent organic nanoprobes with intense blue, green, and orange-red emissions prepared by self-assembling three carbazole derivatives into nanorods/nanoparticles. The three compounds consist of two or four electron-donating carbazole groups linked to a central dicyanobenzene electron acceptor. Steric hindrance from the carbazole groups leads to noncoplanar 3D molecular structures favorable to fluorescence in the solid state, while the donor-acceptor structures endow the molecules with good two-photon excited emission properties. The fluorescent organic nanoprobes exhibit good water dispersibility, low cytotoxicity, superior resistance against photodegradation and photobleaching. Both one- and two-photon fluorescent imaging were shown in the A549 cell line. Two-photon fluorescence imaging with the fluorescent probes was demonstrated to be more effective in visualizing and distinguishing cellular details compared to conventional one-photon fluorescence imaging.

Keywords: carbazole derivatives; electron donor−acceptor; fluorescent organic nanoprobes; self-assembly; two-photon cellular imaging.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbazoles
  • Electrons
  • Fluorescent Dyes
  • Nanostructures*
  • Photons

Substances

  • Carbazoles
  • Fluorescent Dyes