Aryleneethynylenes have been studied for years for both their electronic properties and their conformational flexibility. Control over the conformations of these conjugated systems allows access to molecules with desirable electronic properties. Previously, hydrogen bonding and transition metal coordination have been used as tools to alter the electronic properties of aryleneethynylene systems. In this study, halogen bonding is used to enforce planarity in molecules of this type. The result of this increased coplanarity is enhanced effective conjugation of the unsaturated backbone. Comparisons of electronic spectra of molecules with restricted rotation due to intramolecular halogen bonding and isomeric molecules that are not restricted by this intramolecular attraction demonstrate that a halogen bond can be used to bias the conformational preference of an aryleneethynylene structure. This type of control could potentially lead to the ability to tune the electronic properties of a variety unsaturated organic compounds.<br/><br/>

Manipulating the electronic properties of aryleneethynylenes with halogen bonding

249th National Meeting (2015)

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