Collect. Czech. Chem. Commun. 2002, 67, 1373-1382

2,2':6',2''-Terpyridine as Monodentate Ligand: Halogen Bonding Driven Formation of Discrete 2 : 1 Aggregates with 1,2,4,5-Tetrafluoro-3,6-diiodobenzene

Rosalba Liantonioa, Thomas A. Logothetisa, Maria T. Messinaa, Pierangelo Metrangoloa,*, Alessandra De Santisa, Tullio Pilatib and Giuseppe Resnatia,*

a Politecnico di Milano, Dipartimento di Chimica, Materiali ed Ingegneria Chimica "Giulio Natta", Via Mancinelli 7, I-20131 Milano, Italy
b C.N.R. - Istituto di Scienze e Tecnologie Molecolari, Università di Milano, Via Golgi 19, I-20133 Milano, Italy


2,2':6',2''-Terpyridine (1) is a well-known electron donor module in metal coordination chemistry and typically works as a tridentate ligand. Here it is shown that 1 can also work as electron donor towards iodoperfluorocarbons both in solution and in the solid phase. Halogen-bonded supramolecular systems are thus obtained. Specifically, terpyridine 1 self-assembles with 1,2,4,5-tetrafluoro-3,6-diiodobenzene (2) and affords the trimeric adduct 3, which is stable and crystalline in the air at room temperature. Single crystal X-ray analysis shows how in adduct 3 both iodine atoms of one molecule of 2 are halogen-bonded to the nitrogen atoms of external pyridine rings of two molecules of 1 that act as monodentate electron donors.

Keywords: Halogen bonding; Donor-acceptor interactions; Supramolecular chemistry; Perfluorocarbon compounds; Co-crystals; Pyridines; Crystal structure; X-Ray diffraction.

References: 75 live references.