Selective Schiff Base Formation of Group 9 Organometallic Complexes with Functionalized Spirobifluorene Ligands

Author:

Cid-Seara Krystal M.1,Pereira-Cameselle Raquel2,Bolaño Sandra1ORCID,Talavera Maria1ORCID

Affiliation:

1. Departamento de Química Inorgánica, Universidade de Vigo, Campus Universitario, 36310 Vigo, Spain

2. Departamento de Química Orgánica, Universidade de Vigo, Campus Universitario, 36310 Vigo, Spain

Abstract

Organic amines are important compounds present in a wide variety of products, which makes the development of new systems for their detection an interesting field of study. New organometallic complexes of group 9 [MCp*X(2′-R-2-py-SBF)] (M = Ir, Rh; R = H, X = Cl (6), R = H, X = OAc (7), R = CHO, X = Cl (8)), and [IrCp*Cl(2′, 7-diCHO-2-py-SBF)] (9) (Cp* pentamethylcyclopentadienyl, SBF = 9,9’-spirobifluorene) bearing bidentate C–N ligands based on 9,9′-spirobifluorene were obtained and characterized by NMR spectroscopy, mass spectrometry, IR spectroscopy, and X-ray diffraction analysis when possible. The formation of a Schiff base to give complexes with the formula [MCp*Cl(2′-CH=NR-2-py-SBF)] (M = Ir, Rh; R = alkyl or aryl (10–12)), through condensation of an amine, and the aldehyde group present in these new complexes was studied leading to a selective reactivity depending on the nature of the amine and the metal center. While the iridium complexes only react with aromatic amines, the rhodium derivative requires heat for those but can react at room temperature with aliphatic amines.

Funder

Xunta de Galicia

institutional open access Program of University of Vigo and MDPI Editorial

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

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