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

Marco Saccone, Giancarlo Terraneo, Marco Saccone, Franisco Fernandez-Palacio, Antti Siiskonen, Antti Siiskonen, Antti Siiskonen, Pierangelo Metrangolo, Giuseppe Resnati, Arri Priimagi

Risultato della ricerca: Articlepeer review

9 Citazioni (Scopus)


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 originaleEnglish
pagine (da-a)227-233
Numero di pagine7
Stato di pubblicazionePublished - 2017

All Science Journal Classification (ASJC) codes

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  • ???subjectarea.asjc.3100.3107???
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