A novel copper framework with amino tridentate N‐donor ligand as heterogeneous catalyst for ring opening of epoxides

Abstract

A novel metal-organic framework (MOF) [Cu 3 L(2,6-NDC) 2 ]Á0.5DMF (MOF-Cu-1) was synthesized by solvothermal reaction of copper nitrate trihydrate with 2,6-naphthalenedicarboxylic acid (2,6-H 2 NDC) and amino tridentate N-donor containing ligand of N 1 -(4-(1H-imidazol-1-yl)benzyl)-N 1 -(2-aminoethyl)ethane-1,2-diamine (L). MOF-Cu-1 is a three-dimensional (3D) framework with one-dimensional (1D) channels. Because of the high stability of the framework and the existence of amino functional groups, MOF-Cu-1 presents excellent heterogeneous catalytic activity for ring-opening reaction of epoxides by amines and reusability for four cycles with negligible loss of efficiency. K E Y W O R D Samino tridentate N-donor ligand, epoxides, heterogeneous catalyst, metal-organic framework, ring-opening reaction | INTRODUCTIONEpoxides are common organic molecules with wide range of synthetic applications as intermediates in pharmaceutical and agrochemical industries. [1] The classical ring opening approach of epoxides involves heating of epoxides with large excess of amines at elevated temperature and works less well with poor nucleophilic amines, indicating that it is necessary to develop efficient catalysts for the ring opening reaction of epoxides. [2] Some homogeneous catalysts, including metal salts and acid, have already been applied. [3][4][5] However, with the rise of environmental awareness, heterogeneous catalysis has attracted extensive attention owing to the effective

Pillar-Layered Metal-Organic Frameworks for Sensing Specific Amino Acid and Photocatalyzing Rhodamine B Degradation

“…The PXRD patterns were almost maintained in these medium, except for the one in MeOH with slight disturbance. The high stability of 1 may be ascribed to the two-fold interpenetration [ 35 , 36 ].…”

A Multiple Stimuli–Responsive Ag/P/S Complex Showing Solvochromic and Mechanochromic Photoluminescence

“…The TGA curve of 1 · x Sol in a stream of N 2 ( Figure S1, Supplementary Materials ) indicated that all lattice solvent molecules escaped over the range of ambient temperature to 100 °C, while the major structure remained stable until 150 °C. The theoretical electron number (406 electrons in the lattice voids of each cell) reported by the SQUEEZE program matched 11.3 MeOH molecules relative to each major structure [ 40 , 41 ]. Because the desolvation of the solvent molecules at room temperature was quite fast, the TGA measurement of 1 · x Sol ( Figure S1 ) could not give an accurate x value.…”

Cost-effective catalytic epoxide ring-opening reactions using Zr-based MOF MIP-202: a comparative study with UiO-66-(CO 2 H) 2

“…[20]. The experimental results indicate that both MIP and UiO are able to catalyze the ring-opening of epoxides by methanol and aniline nucleophiles under mild conditions.…”

“…Recent innovations, including the deployment of UiO-66 functionalized with thiophene-2carboxamide [20], copper-based MOF equipped with amine-derived tridentate ligands [21], Fe3O4 nanoparticle-supported Mn (II)-azo Schiff complex [22], and Lewis acidic trifluoromethylate ionic liquids have shown potential [23]. Nevertheless, these catalysts do not come without limitations which include prolonged reaction time, the necessity for high catalyst loadings, stability concerns, and environmental implications.…”