Halogen bonding stabilizes a cis-azobenzene derivative in the solid state: A crystallographic study

MARCO SACCONE, Antti Siiskonen, Franisco Fernandez-Palacio, Arri Priimagi, Giancarlo Terraneo, Giuseppe Resnati, Pierangelo Metrangolo

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

Crystals of trans- and cis-isomers of a fluorinated azobenzene derivative have been prepared and characterized by single-crystal X-ray diffraction. The presence of F atoms on the aromatic core of the azobenzene increases the lifetime of the metastable cis-isomer, allowing single crystals of the cis-azobenzene to be grown. Structural analysis on the cis-azobenzene, complemented with density functional theory calculations, highlights the active role of the halogen-bond contact (N...I synthon) in promoting the stabilization of the cis-isomer. The presence of a long aliphatic chain on the azobenzene unit induces a phase segregation that stabilizes the molecular arrangement for both the trans- and cis-isomers. Due to the rarity of cis-azobenzene crystal structures in the literature, our paper makes a step towards understanding the role of non-covalent interactions in driving the packing of metastable azobenzene isomers. This is expected to be important in the future rational design of solid-state, photoresponsive materials based on halogen bonding. We show by single-crystal X-ray diffraction studies and computational analysis that halogen bonding can stabilize a metastable cis-azobenzene derivative in the solid state.
Lingua originaleInglese
pagine (da-a)227-233
Numero di pagine7
RivistaACTA CRYSTALLOGRAPHICA. SECTION B, STRUCTURAL SCIENCE, CRYSTAL ENGINEERING AND MATERIALS
Volume73
Numero di pubblicazione2
DOI
Stato di pubblicazionePubblicato - 2017

Keywords

  • azobenzene
  • halogen bonding
  • isomerization
  • Electronic
  • Optical and Magnetic Materials
  • Atomic and Molecular Physics
  • and Optics
  • 2506
  • Materials Chemistry2506 Metals and Alloys

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