Crystallization-Induced Emissive Invisible Ink

Nicholas Zerby, Orit Malka, Sagarika Bhattacharya, Nila Nandha Kadamannil, Mark Baranov, Raz Jelinek

Research output: Contribution to journalArticlepeer-review

9 Scopus citations


Crystallization-induced emission (CIE) has been reported for a handful of polyaromatic molecules, and this phenomenon has been generally ascribed to blocking of nonradiative energy dissipation pathways through crystalline organizations. Herein, the first use of a single-ring CIE-based “invisible” ink is reported, which can be applied on varied surfaces. The ink comprises (3E)-4-[4-(methylsulfanyl)phenyl]-3-buten-2-one (MSPB), exhibiting remarkable spontaneous water and interface-induced CIE. The molecule, which is synthesized through a facile one-step process, is nonfluorescent when dissolved in polar organic solvents but forms fluorescent crystalline assemblies upon addition of water or upon drying on solid substrates. X-ray diffraction analysis reveals that the fluorescent crystalline structure of MSPB is stabilized both by intermolecular C⋅⋅⋅HO and C⋅⋅⋅Hπ interactions among adjacent molecules. The readily adopted crystalline organization of MSPB facilitates its use as a fluorescent ink on diverse substrates, including paper, metals, polymers, and ceramic surfaces.

Original languageEnglish
Article number1900232
JournalAdvanced Optical Materials
Issue number11
StatePublished - 4 Jun 2019


  • aggregation-induced emission
  • crystallization-induced emission
  • fluorescence quenching
  • self-assembly
  • π−π stacking

ASJC Scopus subject areas

  • Electronic, Optical and Magnetic Materials
  • Atomic and Molecular Physics, and Optics


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