# US 10,309,035 B2 · Method of preparing sample for crystal structure analysis, method of determining absolute configuration of chiral compound, and polynuclear metal complex monocrystal

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- Number: US 10,309,035 B2
- Document ID: US10309035B2
- Status: Granted
- Kind: B2
- Application number: 15/124,897
- Filed: 2015-03-09
- Published: 2017-01-19
- Granted: 2019-06-04
- Earliest claimed: 2014-03-10
- Assignees: The University of Tokyo
- Applicants: The University of Tokyo
- Inventors: Makoto Fujita; Yasuhide Inokuma; Tatsuhiko Arai
- Web page: https://patentgrep.com/patent/US10309035B2

## CPC

- C30B 7/06: using non-aqueous solvents
- C30B 7/14: the crystallising materials being formed by chemical reactions in the solution
- C30B 29/54: Organic compounds
- G01N 1/28: Preparing specimens for investigation {including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q}(mounting specimens on microscopic slides G02B21/34; means for supporting the objects or the materials to be analysed in electron microscopes H01J37/20 {; laboratory gas handling apparatus B01L5/00})
- G01N 23/207: Diffractometry using detectors, e.g. using a probe in a central position and one or more displaceable detectors in circumferential positions
- G01N 2223/60: Specific applications or type of materials
- C30B: SINGLE-CRYSTAL GROWTH (by using ultra-high pressure, e.g. for the formation of diamonds, B01J3/06); UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL (zone-refining of metals or alloys C22B); PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE (casting of metals, casting of other substances by the same processes or devices B22D; working of plastics B29; modifying the physical structure of metals or alloys C21D, C22F); SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE (for producing semiconductor devices or parts thereof H10); APPARATUS THEREFOR
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)

## Abstract

Method for preparing a crystal structure analysis sample for determining an absolute configuration of a chiral compound includes bringing a single crystal of a porous compound into contact with a solvent solution that contains a chiral compound, the single crystal of the porous compound including a three-dimensional framework, and either or both of pores and voids that are defined by the three-dimensional framework, and are three-dimensionally arranged in an ordered manner, the three-dimensional framework being formed by one molecular chain or two or more molecular chains, or formed by one molecular chain or two or more molecular chains, and a framework-forming compound, and comprising a chiral substituent of which the absolute configuration is known, the crystal structure analysis sample having a structure in which molecules of the chiral compound are arranged in either or both of the pores and the voids of the single crystal in an ordered manner.

## Claims

### Claim 1

A method for preparing a crystal structure analysis sample for determining an absolute configuration of a chiral compound, the method comprising bringing a single crystal of a porous compound into contact with a solvent solution that comprises a chiral compound for which the absolute configuration is to be determined, to prepare a crystal structure analysis sample, the single crystal of the porous compound comprising a three-dimensional framework, and either or both of pores and voids that are defined by the three-dimensional framework, and are three-dimensionally arranged in an ordered manner, the three-dimensional framework being formed by one molecular chain or two or more molecular chains, and a framework-forming compound, and comprising a chiral substituent of which the absolute configuration is known, the crystal structure analysis sample having a structure in which molecules of the chiral compound are arranged in either or both of the pores and the voids of the single crystal in an ordered manner.

### Claim 2 (depends on 1)

The method for preparing a crystal structure analysis sample according to claim 1, wherein the porous compound is a polynuclear metal complex that comprises a ligand having two or more coordinating moieties, a metal ion that serves as a center metal, and the framework-forming compound that comprises the chiral substituent of which the absolute configuration is known.

### Claim 3 (depends on 2)

The method for preparing a crystal structure analysis sample according to claim 2, wherein the ligand having two or more coordinating moieties is a tridentate ligand represented by a formula (1),
wherein Ar is a substituted or unsubstituted trivalent aromatic group, X1 to X3 are independently a divalent organic group, or a single bond that directly bonds Ar and or Y1, Y2, or Y3, and Y1 to Y3 are independently a monovalent organic group having a coordinating moiety.

### Claim 4 (depends on 2)

The method for preparing a crystal structure analysis sample according to claim 2, wherein the metal ion that serves as the center metal is an ion of a metal among the metals that respectively belong to Groups 8 to 12 in the periodic table.

### Claim 5 (depends on 1)

The method for preparing a crystal structure analysis sample according to claim 1, wherein the single crystal is brought into contact with the solvent solution that comprises the chiral compound by immersing the single crystal in the solvent solution that comprises the chiral compound.