Synthesis and Characterization of Diketopyrrolopyrrole-Based Aggregation-Induced Emission Nanoparticles for Bioimaging

Geonho Lee, Jongwook Park, Seong Hyun Jang, Sang Yoon Lee, Jihyun Seong, Jae Woong Jung, Kyobum Kim, Tae Gyu Hwang, Jun Choi

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Conventional fluorescent dyes have the property of decreasing fluorescence due to aggregationcaused quenching effects at high concentrations, whereas aggregation-induced emission dyes have the property of increasing fluorescence as they aggregate with each other. In this study, diketopyrrolopyrrole-based long-wavelength aggregation-induced emission dyes were used to prepare biocompatible nanoparticles suitable for bioimaging. Aggregation-induced emission nanoparticles with the best morphology and photoluminescence intensity were obtained through a fast, simple preparation method using an ultrasonicator. The optimally prepared nanoparticles from 3,6-bis(4-((E)-4-(bis(40-(1,2,2-triphenylvinyl)-[1,10-biphenyl]-4-yl)amino)styryl)phenyl)-2,5-dihexyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (DP-R2) with two functional groups having aggregation-induced emission properties and additional donating groups at the end of the triphenylamine groups were considered to have the greatest potential as a fluorescent probe for bioimaging. Furthermore, it was found that the tendency for aggregation-induced emission, which was apparent for the dye itself, became much more marked after the dyes were incorporated within nanoparticles. While the photoluminescence intensities of the dyes were observed to decrease rapidly over time, the prepared nanoparticles encapsulated within the biocompatible polymers maintained their initial optical properties very well. Lastly, when the cell viability test was conducted, excellent biocompatibility was demonstrated for each of the prepared nanoparticles.

Original languageEnglish
Article number2984
JournalMolecules
Volume27
Issue number9
DOIs
StatePublished - 1 May 2022

Keywords

  • aggregation-induced emission
  • bioimaging
  • dispersibility
  • dyes
  • fluorescence
  • nanoparticles

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