ACQ-to-AIE Transformation: Tuning Molecular Packing by Regioisomerization for Two-Photon NIR Bioimaging

Angew Chem Int Ed Engl. 2020 Jul 27;59(31):12822-12826. doi: 10.1002/anie.202005785. Epub 2020 Jun 4.

Abstract

The traditional design strategies for highly bright solid-state luminescent materials rely on weakening the intermolecular π-π interactions, which may limit diversity when developing new materials. Herein, we propose a strategy of tuning the molecular packing mode by regioisomerization to regulate the solid-state fluorescence. TBP-e-TPA with a molecular rotor in the end position of a planar core adopts a long-range cofacial packing mode, which in the solid state is almost non-emissive. By shifting molecular rotors to the bay position, the resultant TBP-b-TPA possesses a discrete cross packing mode, giving a quantum yield of 15.6±0.2 %. These results demonstrate the relationship between the solid-state fluorescence efficiency and the molecule's packing mode. Thanks to the good photophysical properties, TBP-b-TPA nanoparticles were used for two-photon deep brain imaging. This molecular design philosophy provides a new way of designing highly bright solid-state fluorophores.

Keywords: ACQ-to-AIE transformation; aggregation-induced emission; cross packing; regioisomerization; two-photon imaging.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry*
  • Aniline Compounds / radiation effects
  • Animals
  • Brain / diagnostic imaging
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / radiation effects
  • HeLa Cells
  • Humans
  • Isomerism
  • Mice
  • Microscopy, Confocal
  • Microscopy, Fluorescence
  • Nanoparticles / chemistry
  • Nanoparticles / radiation effects
  • Phenazines / chemistry*
  • Phenazines / radiation effects
  • Photons
  • Thiophenes / chemistry*
  • Thiophenes / radiation effects

Substances

  • Aniline Compounds
  • Fluorescent Dyes
  • Phenazines
  • Thiophenes