Single crystal of porous compound, method for assessing quality of single crystal, method for preparing solution including compound to be analyzed, method for producing crystal structure analysis sample, and method for determining molecular structure of compound to be analyzed

Patent metadata

Field	Value
Publication number	US-10487420-B2
Application number	US-201615556930-A
Country	US
Kind code	B2
Filing date	Mar 10, 2016
Priority date	Mar 10, 2015
Publication date	Nov 26, 2019
Grant date	Nov 26, 2019

Abstract

The present invention provides a single crystal of a porous compound, the single crystal being used to produce a crystal structure analysis sample for a compound to be analyzed by contacting the single crystal of the porous compound having a three-dimensional framework and three-dimensionally regularly-arranged pores and/or hollows formed by being divided by the three-dimensional framework with a solution that includes the compound to be analyzed, and arranging molecules of the compound to be analyzed in a regular array in the pores and/or hollows. The single crystal of the porous compound are characterized in that: one side of the single crystal is 10 to 2000 μm; and the single crystal maintains monocrystalline properties even after the single crystal is placed in contact with a solvent that is chemically the same as the solvent of the solution that includes the compound to be analyzed.

First claim

The invention claimed is:

1. A method for determination of whether a single crystal used for producing a crystal structure analysis sample of an analysis target compound is good or bad by bringing a porous compound single crystal having a three-dimensional framework, and having pores and/or voids, which are defined by the three-dimensional framework, that are three-dimensionally arranged in an ordered manner into contact with an analysis target compound-containing solution to arrange molecules of the analysis target compound in the pores and/or the voids in an ordered manner, the method comprising
step (A1): bringing the single crystal into contact with a solvent which is chemically identical to a solvent of the analysis target compound-containing solution; and
step (A2): when the single crystal is confirmed to maintain single crystallinity even after the contact of the single crystal with the solvent in step (A1), determining the single crystal as suitable for producing the crystal structure analysis sample,
wherein the method for confirming the single crystal as maintaining single crystallinity in step (A2) comprises:
(i) confirming an absence of color irregularities or brightness irregularities in the porous compound single crystal by crossed Nicols observation of the porous compound single crystal using a polarization microscope,
dimensionally arranged in an ordered manner into contact with the analysis target compound-containing solution to arrange molecules of the analysis target compound in the pores and/or the voids in an ordered manner, the method comprising
step (B1): bringing the single crystal into contact with a solvent dissolving the analysis target compound, and
step (B2): when the single crystal is confirmed to maintain single crystallinity even after the contact of the single crystal with the solvent in step (B1), determining the solvent as suitable for a solvent of the analysis target compound-containing solution used for producing the crystal structure analysis sample,
wherein the method for determining the solvent as suitable for the solvent of the analysis target compound-containing solution used for producing the crystal structure analysis sample in step (B2) comprises:
(v) confirming an absence of color irregularities or brightness irregularities in the porous compound single crystal by crossed Nicols observation of the porous compound single crystal using a polarization microscope,
(vi) confirming that a rate of change in absorbance of UV-vis absorption spectrum of the single crystal within a wavelength range of 450 to 500 nm is 10% or less between before and after bringing the single crystal into contact with a solvent which is chemically identical to the solvent of the analysis target compound-containing solution,
(vii) confirming that shape retention ratio of the single crystal is 90% or more between before and after an operation of 10 mm parallel shift of the single crystal by exerting a force of 10 −2 N or less on the single crystal using a tungsten steel needle for manipulating the crystal
(ii) confirming that a rate of change in absorbance of UV-vis absorption spectrum of the single crystal within a wavelength range of 450 to 500 nm is 10% or less between before and after bringing the single crystal into contact with the solvent which is chemically identical to the solvent of the analysis target compound-containing solution,
(iii) confirming that shape retention ratio of the single crystal is 90% or more between before and after an operation of 10 mm parallel shift of the single crystal by exerting a force of 10 −2 N or less on the single crystal using a tungsten steel needle for manipulating the crystal (needle diameter=0.1 mm) in the solvent which is chemically identical to the solvent of the analysis target compound-containing solution at a liquid depth of 5 mm, or
(iv) confirming that shape retention ratio of the single crystal is 90% or more between before and after an operation of sucking a solution containing the single crystal and the solvent which is chemically identical to the solvent of the analysis target compound-containing solution at a suction rate of 6 μL/sec using a pipet tip for 20 to 200 μL having an aperture of 250 μm in diameter at a liquid depth of 5 mm, and then discharging the solution containing the single crystal at a discharge rate of 6 μL/sec.

2. A method for preparing an analysis target compound-containing solution used for producing a crystal structure analysis sample of the analysis target compound by bringing a porous compound single crystal having a three-dimensional framework, and having pores and/or voids, which are defined by the three-dimensional framework, that are three-(needle diameter=0.1 mm) in a solvent which is chemically identical to the solvent of the analysis target compound-containing solution at a liquid depth of 5 mm, or
(viii) confirming that shape retention ratio of the single crystal is 90% or more between before and after an operation of sucking a solution containing the single crystal and a solvent which is chemically identical to the solvent of the analysis target compound-containing solution at a suction rate of 6 μL/sec using a pipet tip for 20 to 200 μL having an aperture of 250 μm in diameter at a liquid depth of 5 mm, and then discharging the solution containing the single crystal at a discharge rate of 6 μL/sec.

3. A method for producing a crystal structure analysis sample, comprising
bringing a single crystal, which is confirmed to maintain single crystallinity by the method according to claim 1 , contact with an analysis target compound-containing solution to arrange molecules of an analysis target compound in the pores and/or the voids in an ordered manner.

4. A method for determining a molecular structure of an analysis target compound, comprising
performing crystal structure analysis using a crystal structure analysis sample obtained by a method for producing the crystal structure analysis sample according to claim 3 .

5. The method for determination of whether a single crystal used for producing a crystal structure analysis sample of an analysis target compound is good or bad according to claim 1 ,
wherein a length of one side of the single crystal is 10 to 2000 μm.

6. The method for determination of whether a single crystal used for producing a crystal structure analysis sample of an analysis target compound is good or bad according to claim 5 ,
wherein the analysis target compound-containing solution is obtained by:
step (B1): bringing the single crystal into contact with a solvent dissolving the analysis target compound, and
step (B2): when the single crystal is confirmed to maintain single crystallinity even after the contact of the single crystal with the solvent in step (B1), determining the solvent as suitable for a solvent of the analysis target compound-containing solution used for producing the crystal structure analysis sample,

wherein the method for determining the solvent as suitable for the solvent of the analysis target compound-containing solution used for producing the crystal structure analysis sample in step (B2) comprises:
(v) confirming an absence of color irregularities or brightness irregularities in the porous compound single crystal by crossed Nicols observation of the porous compound single crystal using a polarization microscope,
(vi) confirming that a rate of change in absorbance of UV-vis absorption spectrum of the single crystal within a wavelength range of 450 to 500 nm is 10% or less between before and after bringing the single crystal into contact with a solvent which is chemically identical to the solvent of the analysis target compound-containing solution,
(vii) confirming that shape retention ratio of the single crystal is 90% or more between b

Assignees

• Univ Tokyo

Inventors

• Fujita Makoto
• Inokuma Yasuhide
• DOUMOTO Yuya

Classifications

• G01N23/20008

  Constructional details of analysers, e.g. characterised by X-ray source, detector or optical system; Accessories therefor; Preparing specimens therefor (monochromators for X- rays using crystals G21K1/06) · CPC title

• G01N23/20

  by using diffraction of the radiation by the materials, e.g. for investigating crystal structure; by using scattering of the radiation by the materials, e.g. for investigating non-crystalline materials; by using reflection of the radiation by the materials · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• C30B29/54 Primary

  Organic compounds · CPC title

• G01N21/21

  Polarisation-affecting properties (G01N21/19 takes precedence) · CPC title