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Compound and use thereof UPDATE_EN

Foreign code F190009907
File No. 07835-US
Posted date Aug 26, 2019
Country United States of America
Application number 95850410
Gazette No. 8134017
Date of filing Dec 2, 2010
Gazette Date Mar 13, 2012
Title Compound and use thereof UPDATE_EN
Abstract A compound represented by the following formula (1) or (2):
Outline of related art and contending technology BACKGROUND ART
Functional dyes are compounds having various characteristics such as a light-emitting property, photoconductivity, light absorptivity, an energy conversion property, and the like. It is expected that, through the use of such physical properties and reactivity, the functional dyes be applied to cutting-edge fields such as electronics, photonics, and molecular imaging, in particular, information recording that responds to external light, heat, pressure, electric field, and the like, information display, energy conversion, medical diagnosing, agricultural and gardening fields, and the like.
Rhodamine dyes, which are one of the most famous functional dyes, are pi-electron organic dyes having characteristics of: (1) emitting fluorescence in a long-wavelength region; (2) having a high fluorescence quantum yield; (3) having a high water-solubility; and (4) having a high resistance to photobleaching. The rhodamine dyes are widely used as fluorescent probes in molecular biology, and widely used in dye-sensitized solar cells, dye lasers and the like, through the use of these characteristics.
However, the rhodamine dyes tend to form aggregates when the rhodamine dye are dissolved in a solution in high concentration or doped on solids. When forming aggregates, the rhodamine dyes form dimers and cause a π-π stacking. At this time, hydrophobic sites of luminophores in molecules overlap each other face-to-face and form non-emission H-type aggregates. As such, the rhodamine dyes have a problem that due to aggregation under the high-concentration condition, luminous efficiency, color development, photosensitivity, and photosensitization are decreased. Note that, the decrease in the functionality due to the aggregation is a phenomenon that conventional organic functional dyes exhibit, and occurs regardless of whether the functional dyes are rhodamine dyes or not. This phenomenon is the largest factor that limits an applicable range of the functional dyes.
In view of the above problems, Tang and others have reported that a Silole compound exhibits AIEE, i.e., emits light when forming aggregates (Y. Hong, J. W. Y. Lam and B. Z. Tang, Chem. Commun., 4332-4353 (2009)). According to the report of Tang and others, various derivatives are produced. However, these compounds still exhibit low fluorescence quantum yield. That is, no pi-electron AIEE molecule having a high luminous efficiency has been developed so far.
Scope of claims [claim1]
1. A compound represented by the following formula (1) or (2):
wherein in the formulae (1) and (2), each R1 independently represents a C1 to C8 alkyl group (which may have a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom), or a hydrogen atom; each R2 independently represents a C1 to C8 alkyl group (which may have a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom), a halogen atom, a nitro group, a carboxyl group, an amino group, or a hydrogen atom; each R3 and each R4 independently represent a C1 to C8 alkyl group (which may have a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom), an allyl group, an aryl group, or a hydrogen atom; each R5 and each R6 independently represent a C1 to C8 alkyl group (which may have a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom), an allyl group, a halogen atom, or a hydrogen atom; and R3 and R5, and/or R4 and R6 may be bound to each other to form a ring, and in the formula (2), each R7 independently represents a C1 to C8 alkyl group (which may have a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom), an amino group, an amide group which may have a protective group or a substituent, a halogen atom, or a hydrogen atom; and R1 and R7 may be bound to each other to form a ring.

[claim2]
2. The compound as set forth in claim 1, represented by any one of the following formulae (3) to (22):
wherein each R and each R11 independently represent a C1 to C8 alkyl group (which may have a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom) or a hydrogen atom; and each R21 independently represents a C1 to C8 alkyl group (which may have a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom), a halogen atom, a nitro group, a carboxyl group, an amino group, or a hydrogen atom.

[claim3]
3. A method for producing a compound, comprising the step of carrying out a condensation process of condensing 2 equivalents of a benzophenone derivative and 1 equivalent of resorcinol in the presence of Lewis acid.

[claim4]
4. The method as set forth in claim 3, further comprising the steps of:
(a) adjusting a solution containing a reactant prepared in the condensation process so that the solution becomes basic;
(b) mixing the solution with an organic solvent to extract the reactant into an organic phase; and
(c) separating the reactant from the organic phase.

[claim5]
5. The method as set forth in claim 4, wherein:
the step (c) separates the reactant from the organic phase as a lactonoid form.

[claim6]
6. The method as set forth in claim 3, wherein:
the benzophenone derivative is a compound represented by the following formula (23):
wherein R1 represents a C1 to C8 alkyl group (which may have a nitrogen atom, oxygen atom, or a sulfur atom as a heteroatom), or a hydrogen atom; R2 represents a C1 to C8 alkyl group (which may have a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom), a halogen atom, a nitro group, a carboxyl group, an amino group, or a hydrogen atom; R3 and R4 each independently represent a C1 to C8 alkyl group (which may have a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom), an allyl group, an aryl group, or a hydrogen atom; R5 and R6 each independently represent a C1 to C8 alkyl group (which may have a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom), an allyl group, a halogen atom, or a hydrogen atom; and R3 and R5, and/or R4 and R6 may be bound to each other to form a ring.

[claim7]
7. A fluorescence emission method comprising the step of causing a compound as set forth in claim 1 to aggregate.

[claim8]
8. A quenching method for quenching emission of fluorescence, comprising the step of eliminating aggregation of a compound as set forth in claim 1.

[claim9]
9. A labeling kit comprising a compound as set forth in claim 1.

[claim10]
10. A labeling method for labeling, by use of a compound as set forth in claim 1, a biological molecule selected from the group consisting of antibodies, peptides, nucleotides, and sugars.

[claim11]
11. An analysis method for analyzing an aggregation mechanism of a target protein, which is labeled by a compound as set forth in claim 1, said method comprising the step of detecting emission of fluorescence.

[claim12]
12. A fluorescent probe comprising:
a biological molecule selected from the group consisting of antibodies, peptides, nucleotides, and sugars; and
a compound as set forth in claim 1.

[claim13]
13. A method for producing a fluorescent probe, said method comprising the step of labeling, by use of a compound as set forth in claim 1, a biological molecule selected from the group consisting of antibodies, peptides, nucleotides, and sugars.

[claim14]
14. A fluorescence imaging method comprising the step of visualizing a diseased portion by fluorescence by administering to a patient a fluorescent probe including a compound as set forth in claim 1 and a biological molecule selected from the group consisting of antibodies, peptides, nucleotides, and sugars.

[claim15]
15. The fluorescence imaging method as set forth in claim 14, wherein:
the biological molecule is a substance that recognizes cancer, and the disease is cancer.

[claim16]
16. A medicine for photodynamic therapy, comprising a compound as set forth in claim 1.

[claim17]
17. The medicine as set forth in claim 16, which is a medicine for treating cancer.

[claim18]
18. A method for treating cancer by photodynamic therapy by administering to a patient a compound as set forth in claim 1.

[claim19]
19. A dye-sensitized solar cell comprising a compound as set forth in claim 1 as a light-absorbing organic-dye material.

[claim20]
20. A light-emitting device comprising a compound as set forth in claim 1.
  • Inventor, and Inventor/Applicant
  • Kamino Shinichiro
  • Enomoto Shuichi
  • RIKEN
IPC(International Patent Classification)

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