Site-selective Assembly between 1,8-Diiodoperfluorooctane and 4,7,8,11-Tetraazahelicene driven by Halogen Bonding

Serena Biella (1) , Massimo Cametti (1) , Tullio Caronna (2) , Gabriella Cavallo (1) , Alessandra Forni (3) , Pierangelo Metrangolo (1) , Tullio Pilati (3) , Giuseppe Resnati (1) , Giancarlo Terraneo (1)

1 POLIMI - Politecnico di Milano [Milan]
2 UniBg - Università degli Studi di Bergamo = University of Bergamo
3 ISTM-CNR

The X-ray diffraction analysis on single crystals obtained from the self-assembly of 1,8 diiodoperfluorooctane 1 with the tetraazahelicene derivative 2 revealed a site-selective pattern of halogen bonds (XBs) in the solid state. Indeed, two non-equivalent halogen bonds drive the formation of an indefinitely repeating pentameric (1)3∙(2)2 unit. Interestingly, the N∙∙∙I-C bonding formation occurred selectively on the pyridazinic/cinnolinic nitrogen atoms of the tetraazahelicene unit, which were preferred over the pyridinic/quinolinic ones. On the basis of MEP and MO analyses, DFT calculations predicted and explained well this site-selective XB formation, thus demonstrating to be efficient tools for the prediction of the XB site-selectivity in similar polynitrogen systems.

Mots clés: Physical Sciences

Domaines: Autre

Serena Biella, Massimo Cametti, Tullio Caronna, Gabriella Cavallo, Alessandra Forni, et al.. Site-selective Assembly between 1,8-Diiodoperfluorooctane and 4,7,8,11-Tetraazahelicene driven by Halogen Bonding. Supramolecular Chemistry, 2011, 23 (03-04), pp.256-262. ⟨10.1080/10610278.2010.521841⟩. ⟨hal-00687342⟩