Complex crystal and chemosensor provided with same

Patent metadata

Field	Value
Publication number	US-11434213-B2
Application number	US-201816493675-A
Country	US
Kind code	B2
Filing date	Mar 15, 2018
Priority date	Mar 16, 2017
Publication date	Sep 6, 2022
Grant date	Sep 6, 2022

Abstract

The complex crystal of the present disclosure is a complex crystal having a structure in which supramolecular units each composed of two or more types of molecules are arrayed. Each of the supramolecular units contains a cyanoacrylic acid derivative and a trisubstituted methylamine as the molecules. The complex crystal has, between the supramolecular units, molecular cavities in each of which a guest molecule for which the supramolecular unit is a host is not disposed. The complex crystal of the present disclosure can have a property of incorporating a chemical substance therein and can exhibit a great change in a characteristic when incorporating the chemical substance therein.

First claim

The invention claimed is:

1. A complex crystal having a structure in which supramolecular units each composed of two or more types of molecules are arrayed, wherein
each of the supramolecular units contains a cyanoacrylic acid derivative and a trisubstituted methylamine as the molecules,
the complex crystal has, between the supramolecular units adjacent to each other:
a guest molecule for which the supramolecular unit is a host; and
molecular cavities in each of which the guest molecule for which the supramolecular unit is the host is not disposed, and
a content of the guest molecules is 1 mol % or less.

2. The complex crystal according to claim 1 , wherein the cyanoacrylic acid derivative is a compound represented by the following formula ( 1 ),

wherein Y is a phenylene group, a naphthylene group, a pyridinylene group, a thiophenylene group, or a furanylene group, each group may have a substituent, R 1 and R 2 are each independently a hydrogen atom, a hydroxyl group, a methoxy group, an ethoxy group, a methyl group, an ethyl group, a propyl group, an isopropyl group, an amino group, a cyano group, an aldehyde group, a thiol group, a vinyl group, a nitro group, a halogen atom, a carboxy ester group, an N-substituted amide group, a phenyl group, a naphthyl group, a pyridyl group, a thiophenyl group, or a furanyl group, the compound represented by formula (1) may or may not have a bond at a broken line portion in formula (1), and, when the compound has a bond, the bond is a single bond, —CH 2 —, —O—, —S—, or —NH—.

3. The complex crystal according to claim 1 , wherein the trisubstituted methylamine is a compound represented by the following formula (2),

wherein R 3 to R 5 are each independently a phenyl group, a naphthyl group, a pyridyl group, a thiophenyl group, or a furanyl group, and each group may have a substituent.

4. The complex crystal according to claim 1 , wherein the complex crystal is obtained by detaching the guest molecules from a precursor complex crystal having a structure in which the supramolecular units and the guest molecules are arrayed, by supercritical drying using supercritical carbon dioxide.

5. A chemosensor comprising:
the complex crystal according to claim 1 ; and
a detection unit configured to detect a characteristic of the complex crystal, wherein
the chemosensor detects a predetermined chemical substance on the basis of a change in the characteristic detected by the detection unit.

6. The chemosensor according to claim 5 , wherein
the detection unit includes a light source configured to irradiate the complex crystal with light, and a light detector configured to detect light emitted from the complex crystal, and
with the light emitted from the complex crystal as the characteristic, the chemosensor detects the predetermined chemical substance on the basis of a change in the light.

7. The chemosensor according to claim 6 , wherein the change in the light is a difference between light emitted from the complex crystal in a first environmental condition and light emitted from the complex crystal in a second environmental condition.

8. A method for producing the complex crystal according to claim 1 , the method comprising
detaching the guest molecules from a precursor complex crystal having a structure in which the supramolecular units and the guest molecules are arrayed, to form the complex crystal, wherein
the detachment of the guest molecules from the precursor complex crystal is carried out by supercritical drying using supercritical carbon dioxide, and
the complex crystal has, between the supramolecular units adjacent to each other:
the guest molecules for which the supramolecular unit is the host and
the molecular cavities in each of which the guest molecule for which the supramolecular unit is the host is not disposed, and
the content of the guest molecules is 1 mol % or less.

9. The complex crystal according to claim 1 , wherein a cavity rate of the complex crystal is equal to or greater than 70%, wherein the cavity rate is a ratio of a number of the molecular cavities in which the guest molecules are not disposed to a sum of a number of the guest molecules and the number of the cavities in which the guest molecules are not disposed.

Assignees

• Panasonic Corp
• Panasonic Holdings Corp

Inventors

• Hosokawa Teppei
• Tohnai Norimitsu
• Nishitani Mikihiko

Classifications

• C07C211/27 Primary

  having amino groups linked to the six-membered aromatic ring by saturated carbon chains · CPC title

• C07D213/74

  Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals · CPC title

• B01J20/22

  comprising organic material · CPC title

• C07D279/26

  without other substituents attached to the ring system · CPC title

• C07D213/38

  having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom · CPC title