Polymorphism, fluorescence, and optoelectronic properties of a borazine derivative

Simon Kervyn De Meerendre, Oliver Fenwick, Francesco Di Stasio, Yong Sig Shin, Johan Wouters, Gianluca Accorsi, Silvio Osella, David Beljonne, Franco Cacialli, Davide Bonifazi

Research output: Contribution to journalArticle

Abstract

We have prepared a new borazine derivative that bears mesityl substituents at the boron centers and displays exceptional chemical stability. Detailed crystallographic and solid-state fluorescence characterizations revealed the existence of several polymorphs, each of which showed different emission profiles. In particular, a bathochromic shift is observed when going from the lower- to the higher-density crystal. Computational investigations of the conformational dynamics of borazine 1 in both the gas phase and in the solid state using molecular dynamics (MD) simulations showed that the conformation of the peripheral aryl groups significantly varies when going from an isolated molecule (in which the rings are able to flip over the 90° barrier at RT) to the crystals (in which the rotation is locked by packing effects), thus generating specific nonsymmetric intermolecular interactions in the different polymorphs. To investigate the optoelectronic properties of these materials by fabrication and characterization of light-emitting diodes (LEDs) and light-emitting electrochemical cells (LECs), borazine 1 was incorporated as the active material in the emissive layer. The current and radiance versus voltage characteristics, as well as the electroluminescence spectra reported here for the first time are encouraging prospects for the engineering of future borazine-based devices.

Original languageEnglish
Pages (from-to)7771-7779
Number of pages9
JournalChemistry: A European Journal
Volume19
Issue number24
DOIs
Publication statusPublished - 10 Jun 2013

Keywords

  • boron
  • doping
  • molecular modeling
  • nitrogen
  • polymorphism

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  • Equipment

  • Datasets

    CCDC 897039: Experimental Crystal Structure Determination

    Kervyn, S. (Contributor), Fenwick, O. (Contributor), Di Stasio, F. (Contributor), Shin, Y. S. (Contributor), WOUTERS, J. (Contributor), Accorsi, G. (Contributor), Osella, S. (Contributor), Beljonne, D. (Contributor), CACIALLI, F. (Contributor) & BONIFAZI, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2013

    Dataset

    CCDC 897046: Experimental Crystal Structure Determination

    Kervyn, S. (Contributor), Fenwick, O. (Contributor), Di Stasio, F. (Contributor), Shin, Y. S. (Contributor), WOUTERS, J. (Contributor), Accorsi, G. (Contributor), Osella, S. (Contributor), Beljonne, D. (Contributor), CACIALLI, F. (Contributor) & BONIFAZI, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2013

    Dataset

    CCDC 897040: Experimental Crystal Structure Determination

    Kervyn, S. (Contributor), Fenwick, O. (Contributor), Di Stasio, F. (Contributor), Shin, Y. S. (Contributor), WOUTERS, J. (Contributor), Accorsi, G. (Contributor), Osella, S. (Contributor), Beljonne, D. (Contributor), CACIALLI, F. (Contributor) & BONIFAZI, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2013

    Dataset

    Cite this

    Kervyn De Meerendre, S., Fenwick, O., Di Stasio, F., Shin, Y. S., Wouters, J., Accorsi, G., Osella, S., Beljonne, D., Cacialli, F., & Bonifazi, D. (2013). Polymorphism, fluorescence, and optoelectronic properties of a borazine derivative. Chemistry: A European Journal, 19(24), 7771-7779. https://doi.org/10.1002/chem.201204598