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

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Halogen bonding stabilizes a cis-azobenzene derivative in the solid state : A crystallographic study. / Saccone, Marco; Siiskonen, Antti; Fernandez-Palacio, Franisco; Priimägi, Arri; Terraneo, Giancarlo; Resnati, Giuseppe; Metrangolo, Pierangelo.

In: ACTA CRYSTALLOGRAPHICA SECTION B : STRUCTURAL SCIENCE, CRYSTAL ENGINEERING AND MATERIALS, Vol. 73, No. 2, 01.04.2017, p. 227-233.

Research output: Contribution to journalArticleScientificpeer-review

Harvard

Saccone, M, Siiskonen, A, Fernandez-Palacio, F, Priimägi, A, Terraneo, G, Resnati, G & Metrangolo, P 2017, 'Halogen bonding stabilizes a cis-azobenzene derivative in the solid state: A crystallographic study', ACTA CRYSTALLOGRAPHICA SECTION B : STRUCTURAL SCIENCE, CRYSTAL ENGINEERING AND MATERIALS, vol. 73, no. 2, pp. 227-233. https://doi.org/10.1107/S2052520617003444

APA

Saccone, M., Siiskonen, A., Fernandez-Palacio, F., Priimägi, A., Terraneo, G., Resnati, G., & Metrangolo, P. (2017). Halogen bonding stabilizes a cis-azobenzene derivative in the solid state: A crystallographic study. ACTA CRYSTALLOGRAPHICA SECTION B : STRUCTURAL SCIENCE, CRYSTAL ENGINEERING AND MATERIALS, 73(2), 227-233. https://doi.org/10.1107/S2052520617003444

Vancouver

Saccone M, Siiskonen A, Fernandez-Palacio F, Priimägi A, Terraneo G, Resnati G et al. Halogen bonding stabilizes a cis-azobenzene derivative in the solid state: A crystallographic study. ACTA CRYSTALLOGRAPHICA SECTION B : STRUCTURAL SCIENCE, CRYSTAL ENGINEERING AND MATERIALS. 2017 Apr 1;73(2):227-233. https://doi.org/10.1107/S2052520617003444

Author

Saccone, Marco ; Siiskonen, Antti ; Fernandez-Palacio, Franisco ; Priimägi, Arri ; Terraneo, Giancarlo ; Resnati, Giuseppe ; Metrangolo, Pierangelo. / Halogen bonding stabilizes a cis-azobenzene derivative in the solid state : A crystallographic study. In: ACTA CRYSTALLOGRAPHICA SECTION B : STRUCTURAL SCIENCE, CRYSTAL ENGINEERING AND MATERIALS. 2017 ; Vol. 73, No. 2. pp. 227-233.

Bibtex - Download

@article{cd4060f6140a43c99e91c4c849e3dd1d,
title = "Halogen bonding stabilizes a cis-azobenzene derivative in the solid state: A crystallographic study",
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.",
keywords = "azobenzene, halogen bonding, isomerization",
author = "Marco Saccone and Antti Siiskonen and Franisco Fernandez-Palacio and Arri Priim{\"a}gi and Giancarlo Terraneo and Giuseppe Resnati and Pierangelo Metrangolo",
year = "2017",
month = "4",
day = "1",
doi = "10.1107/S2052520617003444",
language = "English",
volume = "73",
pages = "227--233",
journal = "ACTA CRYSTALLOGRAPHICA SECTION B : STRUCTURAL SCIENCE, CRYSTAL ENGINEERING AND MATERIALS",
issn = "2052-5192",
publisher = "International Union of Crystallography",
number = "2",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Halogen bonding stabilizes a cis-azobenzene derivative in the solid state

T2 - A crystallographic study

AU - Saccone, Marco

AU - Siiskonen, Antti

AU - Fernandez-Palacio, Franisco

AU - Priimägi, Arri

AU - Terraneo, Giancarlo

AU - Resnati, Giuseppe

AU - Metrangolo, Pierangelo

PY - 2017/4/1

Y1 - 2017/4/1

N2 - 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.

AB - 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.

KW - azobenzene

KW - halogen bonding

KW - isomerization

U2 - 10.1107/S2052520617003444

DO - 10.1107/S2052520617003444

M3 - Article

VL - 73

SP - 227

EP - 233

JO - ACTA CRYSTALLOGRAPHICA SECTION B : STRUCTURAL SCIENCE, CRYSTAL ENGINEERING AND MATERIALS

JF - ACTA CRYSTALLOGRAPHICA SECTION B : STRUCTURAL SCIENCE, CRYSTAL ENGINEERING AND MATERIALS

SN - 2052-5192

IS - 2

ER -