TY - JOUR
T1 - Multidentate unsymmetrically-substituted Schiff bases and their metal complexes
T2 - Synthesis, functional materials properties, and applications to catalysis
AU - Liu, Xiang
AU - Manzur, Carolina
AU - Novoa, Néstor
AU - Celedón, Salvador
AU - Carrillo, David
AU - Hamon, Jean René
N1 - Funding Information:
Invaluable contributions from talented students and colleagues cited in the references, and financial support from the Fondo Nacional de Desarrollo Científico y Tecnológico [FONDECYT (Chile), Grants nos. 1040851, 1090310, 1130105 and 1140903 (D.C. and C.M.)], FONDEQUIP (Chile) EQM130154, the China Scholarship Council (CSC) from the People's Republic of China (XL), the CONICYT (Chile) for graduate fellowships (NN, SC), the Vicerrectoría de Investigación y Desarrollo, Universidad de Concepción (Chile): Grant VRID INICIACIÓN Cod. 216.021.034-1.0-1.OIN (NN), the Vicerrectoría de Investigación y Estudios Avanzados, Pontificia Universidad Católica de Valparaíso (Chile), the Centre National de la Recherche Scientifique (CNRS) (France), the Université de Rennes 1 (France), and the Chilean-French International Associated Laboratory for “Multifunctional Molecules and Materials” (LIAM3-CNRS N° 1027) are gratefully acknowledged. We also thank Dr. H. Hu (Tuscaloosa, Alabama) for helpful discussions.
Funding Information:
Invaluable contributions from talented students and colleagues cited in the references, and financial support from the Fondo Nacional de Desarrollo Científico y Tecnológico [FONDECYT (Chile), Grants nos. 1040851 , 1090310 , 1130105 and 1140903 (D.C. and C.M.)], FONDEQUIP (Chile) EQM130154 , the China Scholarship Council (CSC) from the People’s Republic of China (XL), the CONICYT (Chile) for graduate fellowships (NN, SC), the Vicerrectoría de Investigación y Desarrollo , Universidad de Concepción (Chile): Grant VRID INICIACIÓN Cod. 216.021.034-1.0-1.OIN (NN), the Vicerrectoría de Investigación y Estudios Avanzados , Pontificia Universidad Católica de Valparaíso (Chile), the Centre National de la Recherche Scientifique (CNRS) (France), the Université de Rennes 1 (France), and the Chilean-French International Associated Laboratory for “Multifunctional Molecules and Materials” (LIAM3-CNRS N° 1027) are gratefully acknowledged. We also thank Dr. H. Hu (Tuscaloosa, Alabama) for helpful discussions.
Publisher Copyright:
© 2017 Elsevier B.V.
PY - 2018/2/15
Y1 - 2018/2/15
N2 - This review focuses on the recent developments of unsymmetrically-substituted multidentate Schiff bases whose steric and electronic characteristics are easily manipulated by selecting suitable condensing aldehydes or ketones and primary amines, and on their metal complexes. After a brief historical introduction, this manuscript is divided in three main sections. In the two first parts, the synthesis, reactivity, functions, and properties of tridentate Schiff base precursors and of quadridentate Schiff base metal complexes, respectively, are discussed through a literature survey including examples of research from the authors’ groups. More specifically, the second section is formed of seven subsections with the synthesis of unsymmetrically-substituted tetradentate Schiff bases and their transition metal (V, Mn, Fe, Co, Ni, Cu, Zn, Ru, Pd, Pt) and uranyl complexes. Emphasis is given to our research work based on ferrocenyl-containing tri- and tetradentate unsymmetrically-substituted Schiff base complexes of Ni(II) and Cu(II) starting from variously substituted ferrocenyl-β-diketones. The unsymmetrically-substituted Schiff base complexes present a wide range of remarkable properties that are also summarized in this section, including structural, biocidal, magnetic, and second-order nonlinear optical properties. The third section is devoted to the catalytic activity of Schiff base metal complexes that is discussed through thirteen major organic reactions, including copper-catalyzed azide–alkyne cycloaddition (CuAAC), Henry and nitro-Mannich reactions, hydrosilylation of ketones, aldol, cyclopropanation and epoxidation reactions, among others.
AB - This review focuses on the recent developments of unsymmetrically-substituted multidentate Schiff bases whose steric and electronic characteristics are easily manipulated by selecting suitable condensing aldehydes or ketones and primary amines, and on their metal complexes. After a brief historical introduction, this manuscript is divided in three main sections. In the two first parts, the synthesis, reactivity, functions, and properties of tridentate Schiff base precursors and of quadridentate Schiff base metal complexes, respectively, are discussed through a literature survey including examples of research from the authors’ groups. More specifically, the second section is formed of seven subsections with the synthesis of unsymmetrically-substituted tetradentate Schiff bases and their transition metal (V, Mn, Fe, Co, Ni, Cu, Zn, Ru, Pd, Pt) and uranyl complexes. Emphasis is given to our research work based on ferrocenyl-containing tri- and tetradentate unsymmetrically-substituted Schiff base complexes of Ni(II) and Cu(II) starting from variously substituted ferrocenyl-β-diketones. The unsymmetrically-substituted Schiff base complexes present a wide range of remarkable properties that are also summarized in this section, including structural, biocidal, magnetic, and second-order nonlinear optical properties. The third section is devoted to the catalytic activity of Schiff base metal complexes that is discussed through thirteen major organic reactions, including copper-catalyzed azide–alkyne cycloaddition (CuAAC), Henry and nitro-Mannich reactions, hydrosilylation of ketones, aldol, cyclopropanation and epoxidation reactions, among others.
KW - Catalysis
KW - Nonlinear optics
KW - Transition metals
KW - Unsymmetrically-substituted Schiff base complexes
KW - Unsymmetrically-substituted tetradentate Schiff base ligands
UR - http://www.scopus.com/inward/record.url?scp=85037376196&partnerID=8YFLogxK
U2 - 10.1016/j.ccr.2017.11.030
DO - 10.1016/j.ccr.2017.11.030
M3 - Review article
AN - SCOPUS:85037376196
VL - 357
SP - 144
EP - 172
JO - Coordination Chemistry Reviews
JF - Coordination Chemistry Reviews
SN - 0010-8545
ER -