Synthesis, crystal structure, polymorphism and microscopic luminescence properties of anthracene derivative compounds

Anna Moliterni, Davide Altamura, Rocco Lassandro, Vincent Olieric, Gianmarco Ferri, Francesco Cardarelli, Andrea Camposeo, Dario Pisignano, John E. Anthony, Cinzia Giannini

Research output: Contribution to journalArticlepeer-review

8 Scopus citations


Anthracene derivative compounds are currently investigated because of their unique physical properties (e.g. bright luminescence and emission tunability), which make them ideal candidates for advanced optoelectronic devices. Intermolecular interactions are the basis of the tunability of the optical and electronic properties of these compounds, whose prediction and exploitation benefit from knowledge of the crystal structure and the packing architecture. Polymorphism can occur due to the weak intermolecular interactions, requiring detailed structural analysis to clarify the origin of observed material property modifications. Here, two silylethyne-substituted anthracene compounds are characterized by single-crystal synchrotron X-ray diffraction, identifying a new polymorph in the process. Additionally, laser confocal microscopy and fluorescence lifetime imaging microscopy confirm the results obtained by the X-ray diffraction characterization, i.e. shifting the substituents towards the external benzene rings of the anthracene unit favours π-π interactions, impacting on both the morphology and the microscopic optical properties of the crystals. The compounds with more isolated anthracene units feature shorter lifetime and emission spectra, more similar to those of isolated molecules. The crystallographic study, supported by the optical investigation, sheds light on the influence of non-covalent interactions on the crystal packing and luminescence properties of anthracene derivatives, providing a further step towards their efficient use as building blocks in active components of light sources and photonic networks.

Original languageEnglish
Pages (from-to)427-435
Number of pages9
JournalActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials
StatePublished - May 8 2020

Bibliographical note

Funding Information:
Funding for this research was provided by: European Research Council under the European Union’s Horizon 2020 Research and Innovation Programme (grant No. 682157 to Andrea Camposeo, Dario Pisignano); Italian Minister of University and Research under the PRIN program (grant No. 201795SBA3 to Andrea Camposeo); US National Science Foundation (grant No. 1849213 to John E. Anthony).

Publisher Copyright:
© 2020.


  • anthracene derivative compounds
  • crystal structure
  • fluorescence lifetime imaging microscopy
  • laser confocal microscopy
  • luminescent compounds
  • optical properties
  • organic semiconductors
  • polymorphism
  • single-crystal diffraction
  • synchrotron data

ASJC Scopus subject areas

  • Electronic, Optical and Magnetic Materials
  • Atomic and Molecular Physics, and Optics
  • Metals and Alloys
  • Materials Chemistry


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