C2 symmetric fluorescent chiral carboxylic acid ligand L-H2 and preparation method and application thereof
A chiral carboxylic acid, L-H2 technology, applied in the fields of coordination chemistry and chiral chemistry, can solve the problems of single chiral separation function, failure to have chiral fluorescence recognition at the same time, etc. Manipulative, easy-to-repeat effects
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Embodiment 1
[0047] a C 2 Symmetric Fluorescent Chiral Carboxylate Ligand L-H 2 The synthesis of its synthetic route such as figure 1 As shown, the specific steps are as follows:
[0048] 1) Dissolve L-phenylalanine and thionyl chloride at a ratio of 1:1 in anhydrous methanol, then stir and react at room temperature for 12 hours, and use 1mol L -1 sodium hydroxide solution to adjust the pH of the reaction mixture to 8, extract the organic phase with ethyl acetate, then dry and concentrate to obtain the crude product of L-phenylalanine methyl ester, the purity of this reaction product can be directly used for the next step Reaction; wherein thionyl chloride needs redistillation and purification treatment, otherwise the reaction is incomplete, resulting in a reduction in yield;
[0049] 2) Dissolve naphthalene-1,5-disulfonyl chloride in CH 2 Cl 2 , add 2.2 times the equivalent of triethylamine, after stirring at room temperature, add L-phenylalanine methyl ester, wherein the ratio of th...
Embodiment 2
[0054] C-based 2 Symmetric Fluorescent Chiral Carboxylate Ligand L-H 2 The synthetic method of the zinc-based chiral porous coordination polymer specifically comprises the following steps:
[0055] Change L-H 2 (11.8mg, 0.02mmol), Zn(NO 3 ) 2 ·6H 2 O (11.9 mg, 0.04 mmol) and 4,4'-bipyridine (bpy) (3.12 mg, 0.02 mmol) were dissolved in 5 mL of a mixture of N, N'-dimethylformamide (DMF) and acetonitrile (MeCN) In solvent (v DMF : v MeCN =1:1), sealed in a 20mL explosion-proof glass bottle, and heated at 60°C for 36 hours to obtain a colorless block crystal of a zinc-based chiral porous coordination polymer with a yield of 60%. IR (KBr tablet, v / cm -1 ): 3358(m), 3339(m), 3073(m), 3055(m), 3012(w), 2909(w), 2344(w), 1633(s), 1533(s), 1433(m) ,1396(m),1342(m),1256(m),1220(m),1190(m),1081(w),1062(w),1038(m),1008(m),977(m) , 899(m), 770(m), 694(m), 674(m), 619(w), 533(w), 472(w). When changing the type of metal salt, the type of solvent or L-H 2 , Zn(NO 3 ) 2 ·6H 2 Th...
Embodiment 3
[0063] Chiral recognition adsorption experiment of styrene oxide
[0064] In view of the open chiral nanopores and abundant chiral recognition sites in zinc-based chiral porous coordination polymers, styrene oxide was used as a substrate to study its ability to selectively recognize different enantiomers.
[0065] The crystals of zinc-based chiral porous coordination polymers were subjected to solvent exchange treatment with methanol and acetone respectively for 2 hours, and 20 mg was placed in an ethanol solution of racemic styrene oxide with a concentration of 1.0 mg / mL, and was analyzed by HPLC Chromatographically measure the enantiomeric excess value (ee.) of styrene oxide in the supernatant at the time of 0h, 1h, 2h and 3h
[0066] The chiral adsorption separation experiment of styrene oxide and its results are as follows: Figure 7 As indicated, the contact time of zinc-based chiral porous coordination polymers with styrene oxide was changed. The ee. values of styren...
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