Multi-directional polydentate ligands for metal-organic hybrid structures

Patent metadata

Field	Value
Publication number	US-10562845-B2
Application number	US-201716085525-A
Country	US
Kind code	B2
Filing date	Jul 28, 2017
Priority date	Jul 29, 2016
Publication date	Feb 18, 2020
Grant date	Feb 18, 2020

Abstract

A compound represented by Chemical Formula 1 according to the present invention can coordinate with metal ions to form a bidirectional or multidirectional metal-organic hybrid structure. Thus, the present invention can synthesize various ligands using amine-aldehyde condensation, and synthesize metal-organic materials using the same.

First claim

The invention claimed is:

1. A compound represented by the following Chemical Formula 1, or a salt thereof:

in the Chemical Formula 1,
each R is independently —R 1 , —NH—CO—R 2 , or —NH—R 2 ,
each R 1 is independently —OH, a C 6-60 aryl, a C 1-10 alkyl, or an amino acid residue, and
each R 2 is a C 1-10 alkyl, a C 6-60 aryl, or a C 4-60 heteroaryl containing one of N, O, and S.

2. The compound according to claim 1 , wherein each R 1 is independently —OH, phenyl, naphthyl, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, or an amino acid residue selected from the group consisting of alanine, cysteine, aspartic acid, glutamic acid, phenylalanine, histidine, isoleucine, lysine, leucine, methionine, asparagine, pyrrolysine, glutamine, arginine, serine, threonine, selenocysteine, valine, tryptophan, and tyrosine.

3. The compound according to claim 1 , wherein each R 2 is independently methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, hexyl, octyl, phenyl, naphthyl, or pyridinyl.

4. The compound according to claim 1 , wherein the compound represented by Chemical Formula 1 is a compound represented by one of the following Chemical Formulas 1-1 to 1-5:

5. A method for preparing a compound represented by the following Chemical Formula 1 comprising the steps of:
1) reacting a compound represented by the following Chemical Formula 1′, a compound represented by the following Chemical Formula 2′ and trifluoroacetic acid to prepare a compound represented by the following Chemical Formula 3; and
2) reacting the compound represented by the following Chemical Formula 3′ with a compound represented by the following Chemical Formula 4′:

in the Chemical Formulas 1 and 4′,
each R is independently —R 1 , —NH—CO—R 2 , or —NH—R 2 ,
each R 1 is independently —OH, a C 6-60 aryl, a C 1-10 alkyl, or an amino acid residue, and
each R 2 is a C 1-10 alkyl, a C 6-60 aryl, or a C 4-60 heteroaryl containing one of N, O, and S.

6. The compound according to claim 5 , wherein each R 1 is independently —OH, phenyl, naphthyl, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, or an amino acid residue selected from the group consisting of alanine, cysteine, aspartic acid, glutamic acid, phenylalanine, histidine, isoleucine, lysine, leucine, methionine, asparagine, pyrrolysine, glutamine, arginine, serine, threonine, selenocysteine, valine, tryptophan, and tyrosine.

7. The compound according to claim 5 , wherein each R 2 is independently methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, hexyl, octyl, phenyl, naphthyl, or pyridinyl.

8. The compound according to claim 5 , wherein the compound represented by Chemical Formula 1 is a compound represented by one of the following Chemical Formulas 1-1 to 1-5:

Assignees

• Lg Chemical Ltd
• Seoul Nat Univ R&Db Foundation

Inventors

• Lee Dongwhan
• Kim Jung Hwan
• Kwon Won Jong
• Bae Yong Jin

Classifications

• C07D251/48

  Two nitrogen atoms · CPC title

• C07D251/24 Primary

  to three ring carbon atoms · CPC title

• C07C251/48

  with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• B01J2531/48

  Zirconium · CPC title