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Aggregation-Induced Enhanced Emission of Tetraphenylethene-phenylalanine Hybrids: Synthesis and Characterization.

Antonia I AntoniouMichela PesentiStefania CrespiDhriti S ShenoyMarta PenconiAlberto BossiSara Pellegrino
Published in: The Journal of organic chemistry (2024)
Aggregation-induced emitting (AIE) luminophores are sensitive and easy-to-handle types of probes that allow driving a stimulus-responsive off/on optical tool through the manipulation of the aggregation behavior. In this work, tetraphenylethene (TPE)-phenylalanine derivatives, characterized by strong aggregation-induced luminescence, were obtained through Suzuki-Miyaura cross-coupling reactions. The reaction proved to be straightforwardly applicable in the single amino acid synthesis as well as in the late-stage peptide functionalization by means of both the classical solution-phase reaction and solid-phase synthesis. A comprehensive structural and analytical investigation highlighted the features driving the self-assembly process and its relationship to AIE efficiency. In particular, we showed that the simple slight (asymmetric) extension of the TPE π-systems results in more efficient and brighter emissions, with respect to the simple TPE system itself.
Keyphrases
  • living cells
  • fluorescent probe
  • amino acid
  • quantum dots
  • small molecule
  • high resolution
  • energy transfer
  • solid state
  • single molecule
  • mass spectrometry
  • high speed
  • cancer therapy
  • drug delivery