Fluorinated azobenzenes with highly strained geometries for halogen bond-driven self-assembly in the solid state. Issue 1 (9th October 2014)

• Record Type: Journal Article
• Authors: Bushuyev, Oleksandr S.; Tan, Davin; Barrett, Christopher J.; Friščić, Tomislav
• Is Part Of: CrystEngComm. Volume 17:Issue 1(2015)
• Page Start: 73
• Page End: 80
• Publication Date: 2014-10-09
• Subjects: Crystals -- Periodicals; Crystal growth -- Periodicals; Crystallography -- Periodicals; Cristaux -- Périodiques; Cristaux -- Croissance -- Périodiques; Cristallographie -- Périodiques; 548
• DOI: 10.1039/c4ce01216j
• Languages: English
• ISSNs: 1466-8033

Abstract

Abstract : Replacing ortho -fluorine substituents on fluorinated azobenzenes with morpholine groups gives conformationally unusual molecules acting as halogen bond donors and acceptors. Abstract : Attempted cocrystallisation of brominated and iodinated octafluoroazobenzene derivatives with morpholine led to the exhaustive replacement of fluorine substituents that are in ortho -positions to the azobenzene with sterically demanding morpholine groups. The resulting molecules exhibit a highly unusual strained conformation of the azobenzene unit, in which the terminal phenyl rings adopt a mutually nearly completely orthogonal orientation. Substitution of ortho -fluorine groups with N -morpholine fragments provides molecules with active halogen bond donor and acceptor sites that guide the molecular self-assembly in the solid state towards the formation of polymeric halogen-bonded chains.