Homochiral Cluster-Organic Frameworks Constructed from Enantiopure Lactate Derivatives

Abstract

Two enantiopure organic linkers ((R)-H 3 CIA and (S)-H 3 CIA) derived from lactic acid have been synthesized and used to construct four pairs of homochiral metal−organic frameworks (HMOFs) with polymetallic building blocks. Crystallographic analysis indicates that H 3 CIA ligands can connect tetranuclear zinc units into kgd type layered structure, whilst the introduction of nitrogen heterocycle auxiliary ligands into this system gives rise to the formation of three-dimensional homochiral MOFs with different structural topologies. Physical characteristics of these complexes are also carried out, including thermal stabilities, solid-state circular dichroism (CD), and photoluminescent properties. Our results highlight the effective method to apply inexpensive and nontoxic chiral ligands to prepare interesting HMOFs.

A pair of novel Cd(II) enantiomers based on lactate derivatives: Synthesis, crystal structures and properties

“…The chiral ligands (R)-H 3 CIA and (S)-H 3 CIA were prepared from L-( À )-lactic acid methyl ester, D-( À )-lactic acid methyl ester and dimethyl 5-hydroxyisophthalate as described previously by our group [6]. The other reagents and solvents were purchased commercially without further purification, unless otherwise indicated.…”

“…However, it is difficult to develop multidimensional HMOFs from these natural products for their flexibility and typical small size [5]. In order to overcome these shortcomings, we have presented a relatively simple and cheap synthesis procedure for chiral ligands ((S)-H 3 CIA and (R)-H 3 CIA) using lactic acid and dimethyl 5-hydroxyisophthalat as starting materials [6]. Containing lactic acid and isophthalate units, (S)-H 3 CIA and (R)-H 3 CIA have provided a feasible approach to construct 3D HMOFs [7].…”

“…Under the hydrothermal condition, a pair of Cd-based HMOFs have been obtained, namely [Cd 2.5 ((R)-CIA) 6 (1,4-DIB)(H 2 O) 2 ] Á ((CH 3 ) 2 NH 2 ) Á H 2 O(1-D) and [Cd 2.5 ((S)-CIA) 6 (1, 4-DIB)(H 2 O) 2 ] Á ((CH 3 ) 2 NH 2 ) Á H 2 O(1-L). Their synthesis, crystal structures, CD spectra, thermal stabilities and luminescent properties are described blow.…”

Synthesis, Structure, and Properties of Cadmium(II) Centered Chiral Coordination Polymer based on (R)‐6‐(1‐Carboxyethoxy)‐2‐naphthoic Acid

“…The properties of chiral coordination polymers are closely related to their structures. The structure of coordination polymers is highly dependent on organic connectors and metal ions, both of which are crucial in the construction of chiral coordination polymers . Utilizing chiral ligands is the most straightforward way to introduce the chirality in coordination polymer , .…”

Synthesis of Metal–Organic Zeolites with Homochirality and High Porosity for Enantioselective Separation

“…9 Among them, three carboxylate groups have multiple coordination modes and the enantiopure lactic acid unit can provide the chiral source for the construction of HMOFs; the oxygen atom of the ether group often participates in building the corresponding HMOFs. Using the pair of ligands with transition metals, we have synthesized a series of HMOFs with intriguing structures and diverse topologies.…”