title: 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.
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.
authors.affiliation: Instituto de Química, Universidade Federal do Rio de Janeiro, Centro Tecnológica, Bloco A, Cidade Universitária, Ilha do Fundão, 21949-909 Rio de Janeiro, RJ, Brazil. garden@iq.ufrj.br.
authors.forename: Ramon
authors.identifier: http://orcid.org/0000-0003-4215-465X
authors.initials: R
authors.lastname: Borges da Silva
authors.affiliation: Instituto de Química, Universidade Federal do Rio de Janeiro, Centro Tecnológica, Bloco A, Cidade Universitária, Ilha do Fundão, 21949-909 Rio de Janeiro, RJ, Brazil. garden@iq.ufrj.br.
authors.forename: Rodolfo Inêz
authors.identifier: http://orcid.org/0000-0001-8042-8442
authors.initials: RI
authors.lastname: Teixeira
authors.affiliation: Instituto de Tecnologia em Fármacos - Farmanguinhos, Fiocruz. R. Sizenando Nabuco, 100, Manguinhos, 21041-250, Rio de Janeiro, RJ, Brazil and Department of Chemistry, University of Aberdeen, Old Aberdeen, AB24 3UE, Scotland, UK.
authors.forename: James L
authors.initials: JL
authors.lastname: Wardell
authors.affiliation: CHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland, UK.
authors.forename: Solange M S V
authors.initials: SM
authors.lastname: Wardell
authors.affiliation: Instituto de Química, Universidade Federal do Rio de Janeiro, Centro Tecnológica, Bloco A, Cidade Universitária, Ilha do Fundão, 21949-909 Rio de Janeiro, RJ, Brazil. garden@iq.ufrj.br.
authors.forename: Simon J
authors.identifier: http://orcid.org/0000-0002-5641-155X
authors.initials: SJ
authors.lastname: Garden