title: Supramolecular hierarchy among halogen-bond donors.
abstract: Through a combination of structural chemistry, vibrational spectroscopy, and theory, we have systematically examined the relative structure-directing importance of a series of ditopic halogen-bond (XB) donors. The molecular electrostatic potential surfaces of six XB donors were evaluated, which allowed for a charge-based ranking. Each molecule was then co-crystallized with 21 XB acceptors and the results have made it possible to map out the supramolecular landscape describing the competition between I/Br-ethynyl donors, perfluorinated I/Br donors, and I/Br-phenyl based donors. The results offer practical guidelines for synthetic crystal engineering driven by robust and directional halogen bonds.
authors.affiliation: Department of Chemistry, Kansas State University, 211 CBC Building, Manhattan, KS 66506 (USA), Fax: (+1) 785-532-6666. aakeroy@k-state.edu.
authors.forename: Christer B
authors.initials: CB
authors.lastname: Aakeröy
authors.forename: Michele
authors.initials: M
authors.lastname: Baldrighi
authors.forename: John
authors.initials: J
authors.lastname: Desper
authors.forename: Pierangelo
authors.initials: P
authors.lastname: Metrangolo
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Resnati
keywords: crystal engineering; donor-acceptor systems; halogen bonding; self-assembly; supramolecular chemistry