The iodoalkynyl group is a ditopic synthon, able to act as a halogen bond (XB) donor through the iodine atom and as an XB acceptor on the C≡C triple bond. With the aim of exploring the self-assembly properties via XB of calix[4]arene macrocycles containing this synthon, we synthesized and characterized a tetra(iodopropargyl)calix[4]arene (3). In the solid state, all the iodoalkynyl units of 3 are involved in intermolecular XB interactions as both donors and acceptors, resulting in a two-dimensional network of calixarene double layers. On the contrary, in the cocrystal of 3 with 4,4′-bipyridine, a bidentate XB acceptor, the iodine atoms are halogen bonded to the pyridine nitrogen atoms forming a one-dimensional ribbon of calixarenes alternated by two 4,4′-bipyridine units. These supramolecular architectures are the first example of solid-state networks of calixarene derivatives where the self-assembly is mostly driven by XBs.

Halogen bonds direct the solid state architectures of a multivalent iodopropargylcalix[4]arene / Gullo, MARIA CHIARA; Baldini, Laura; Casnati, Alessandro; Marchio', Luciano. - In: CRYSTAL GROWTH & DESIGN. - ISSN 1528-7483. - 20:6(2020), pp. 3611-3616. [10.1021/acs.cgd.0c00442]

Halogen bonds direct the solid state architectures of a multivalent iodopropargylcalix[4]arene

Maria Chiara Gullo;Laura Baldini;Alessandro Casnati;Luciano Marchiò
2020-01-01

Abstract

The iodoalkynyl group is a ditopic synthon, able to act as a halogen bond (XB) donor through the iodine atom and as an XB acceptor on the C≡C triple bond. With the aim of exploring the self-assembly properties via XB of calix[4]arene macrocycles containing this synthon, we synthesized and characterized a tetra(iodopropargyl)calix[4]arene (3). In the solid state, all the iodoalkynyl units of 3 are involved in intermolecular XB interactions as both donors and acceptors, resulting in a two-dimensional network of calixarene double layers. On the contrary, in the cocrystal of 3 with 4,4′-bipyridine, a bidentate XB acceptor, the iodine atoms are halogen bonded to the pyridine nitrogen atoms forming a one-dimensional ribbon of calixarenes alternated by two 4,4′-bipyridine units. These supramolecular architectures are the first example of solid-state networks of calixarene derivatives where the self-assembly is mostly driven by XBs.
2020
Halogen bonds direct the solid state architectures of a multivalent iodopropargylcalix[4]arene / Gullo, MARIA CHIARA; Baldini, Laura; Casnati, Alessandro; Marchio', Luciano. - In: CRYSTAL GROWTH & DESIGN. - ISSN 1528-7483. - 20:6(2020), pp. 3611-3616. [10.1021/acs.cgd.0c00442]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2881952
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