Copper(ii) catalyzed synthesis of novel helical luminescent benzo[4, 5]imidazo[1, 2-a][1, 10]phenanthrolines via an intramolecular C–H amination reaction. Issue 4 (19th December 2016)

• Record Type: Journal Article
• Authors: Borges da Silva, Ramon; Teixeira, Rodolfo Inêz; Wardell, James L.; Wardell, Solange M. S. V.; Garden, Simon J.
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 4(2017)
• Page Start: 812
• Page End: 826
• Publication Date: 2016-12-19
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob02508k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Novel helical luminescent benzoimidazophenanthrolines were prepared using a Cu(ii ) catalyzed C–H amination reaction. Abstract : In the present study a series of N -phenyl-1, 10-phenanthroline-2-amine derivatives were obtained by heating 2-chlorophenanthroline with aniline derivatives under solvent free conditions in good to excellent yields. The N -phenyl-1, 10-phenanthroline-2-amines were employed as substrates in a copper(ii )-catalyzed C–H amination reaction to give derivatives of the novel heterocyclic system benzo[4, 5]imidazo[1, 2- a ][1, 10]phenanthroline. The structure of these compounds was predicted to be helical by DFT calculations and single crystal X-ray diffraction of an example of this system confirmed the non-planar helical structure. The luminescence properties of the parent heterocyclic system were characterized.