Intermolecular interactions-photophysical properties relationships in phenanthrene-9,10-dicarbonitrile assemblies

Anastasiia M. Afanasenko, Alexander S. Novikov, Tatiana G. Chulkova*, Yakov M. Grigoriev, Ilya E. Kolesnikov, Stanislav Selivanov, Galina L. Starova, Andrey A. Zolotarev, Anatoly N. Vereshchagin, Michail N. Elinson

*Corresponding author for this work

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Abstract

Phenanthrene-9,10-dicarbonitriles show various luminescence behaviour in solution and in the solid state. Aggregation patterns of phenanthrene-9,10-dicarbonitriles govern their luminescent properties in the solid state. Single crystal structures of phenanthrene-9,10-dicarbonitriles showed head-to-tail intraplane (or quasi-intraplane) intermolecular interactions and π-stacking patterns with eclipsing of molecules when viewed orthogonal to the stacking plane. The π-stacking interactions were detected in the X-ray structures of phenanthrene-9,10-dicarbonitriles and studied by DFT calculations at the M06–2X/6–311++G(d,p) level of theory and topological analysis of the electron density distribution within the framework of QTAIM method. The estimated strength of the C⋯C contacts responsible for the π-stacking interactions is 0.6–1.1 kcal/mol. The orientation of molecules in crystals depends on the substituents in phenanthrene-9,10-dicarbonitriles. Distinct molecular orientation and packing arrangements in crystalline phenanthrene-9,10-dicarbonitriles ensured perturbed electronic communication among the nearest and non-nearest molecules through an interplay of excimer and dipole couplings. As a result, the intermolecular interactions govern the solid state luminescence of molecules.

Original languageEnglish
Article number126789
Number of pages8
JournalJournal of Molecular Structure
Volume1199
DOIs
Publication statusPublished - 5-Jan-2020

Keywords

  • Phenanthrene-9,10-dicarbonitriles
  • DFT studies
  • Fluorescence
  • pi-Stacking
  • NONCOVALENT INTERACTIONS
  • OPTICAL-PROPERTIES
  • MEROCYANINE DYES
  • SOLID-STATE
  • PI-STACKING
  • FLUORESCENCE
  • HALOGEN
  • TRANSFORMATION
  • ABSORPTION
  • GENERATION
  • CCDC 1821026: Experimental Crystal Structure Determination

    Afanasenko, A. (Contributor), Novikov, A. S. (Contributor), Chulkova, T. G. (Contributor), Grigoriev, Y. M. (Contributor), Kolesnikov, I. E. (Contributor), Selivanov, S. I. (Contributor), Starova, G. L. (Contributor), Zolotarev, A. A. (Contributor), Vereshchagin, A. N. (Contributor) & Elinson, M. N. (Contributor), University of Groningen, 31-Jan-2018

    Dataset

  • CCDC 1820117: Experimental Crystal Structure Determination

    Afanasenko, A. (Contributor), Novikov, A. S. (Contributor), Chulkova, T. G. (Contributor), Grigoriev, Y. M. (Contributor), Kolesnikov, I. E. (Contributor), Selivanov, S. I. (Contributor), Starova, G. L. (Contributor), Zolotarev, A. A. (Contributor), Vereshchagin, A. N. (Contributor) & Elinson, M. N. (Contributor), University of Groningen, 29-Jan-2018

    Dataset

  • CCDC 1821025: Experimental Crystal Structure Determination

    Afanasenko, A. (Contributor), Novikov, A. S. (Contributor), Chulkova, T. G. (Contributor), Grigoriev, Y. M. (Contributor), Kolesnikov, I. E. (Contributor), Selivanov, S. I. (Contributor), Starova, G. L. (Contributor), Zolotarev, A. A. (Contributor), Vereshchagin, A. N. (Contributor) & Elinson, M. N. (Contributor), University of Groningen, 31-Jan-2018

    Dataset

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