Halogen bonding and pi...pi stacking control reactivity in the solid state

Tullio Caronna; Rosalba Liantonio; Thomas A Logothetis; Pierangelo Metrangolo; Tullio Pilati; Giuseppe Resnati

doi:10.1021/ja039884n

Halogen bonding and pi...pi stacking control reactivity in the solid state

J Am Chem Soc. 2004 Apr 14;126(14):4500-1. doi: 10.1021/ja039884n.

Authors

Tullio Caronna¹, Rosalba Liantonio, Thomas A Logothetis, Pierangelo Metrangolo, Tullio Pilati, Giuseppe Resnati

Affiliation

¹ University of Bergamo, Faculty of Engineering, Via Marconi 5, 24044 Dalmine, Bergamo, Italy.

PMID: 15070351
DOI: 10.1021/ja039884n

Abstract

The halogen bonding and the pi...pi stacking interactions induce the noncovalent self-assembly of modules into photoreactive supramolecular architecture. The pi...pi interaction pre-organizes the template, and the halogen bonding aligns the olefins to conform to the topochemical principle for photoreaction. The UV irradiation of the crystal resulted in a cyclization product with quantitative yield and stereospecificity.