Issue 4, 2017

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.

Graphical abstract: 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

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
16 Nov 2016
Accepted
14 Des 2016
First published
14 Des 2016

Org. Biomol. Chem., 2017,15, 812-826

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

R. Borges da Silva, R. I. Teixeira, J. L. Wardell, S. M. S. V. Wardell and S. J. Garden, Org. Biomol. Chem., 2017, 15, 812 DOI: 10.1039/C6OB02508K

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