Switching the Photoluminescence and Electrochemiluminescence of Liposoluble Porphyrin in Aqueous Phase by Molecular Regulation

Angew Chem Int Ed Engl. 2020 Dec 14;59(51):23261-23267. doi: 10.1002/anie.202010216. Epub 2020 Oct 15.

Abstract

By a facile peripheral decoration of 5-(4-aminophenyl)-10,15,20-triphenylporphyrin (ATPP) with inherent aggregation-induced emission (AIE) active tetraphenylethene (TPE), a versatile AIEgenic porphyrin derivative (ATPP-TPE) was obtained, which greatly abolishes the detrimental π-π stacking and thus surmounts the notorious aggregation-caused quenching (ACQ) effect of ATPP in aqueous phase. The photoluminescence of ATPP-TPE is 4.5-fold stronger than ATPP at aggregation state. Moreover, an unequivocal aggregation induced electrochemiluminescence (AIECL) of ATPP-TPE was found to be seriously dependent on its aggregation property in aqueous solution with efficiency of 34 %, which is 6 times higher than pure ATPP. The versatility of this molecular structure modulation strategy along with the ACQ-to-AIE transformation in this work provides direction to guide for applying liposoluble porphyrins in aqueous phase by designs of synthetic porphyrin AIEgens.

Keywords: aqueous phase; electrochemiluminescence; molecular regulation; photoluminescence; porphyrin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Electrochemical Techniques
  • Fluorescent Dyes / analysis*
  • Luminescent Measurements
  • Molecular Structure
  • Photochemical Processes
  • Porphyrins / analysis*
  • Water / chemistry

Substances

  • Fluorescent Dyes
  • Porphyrins
  • Water