Compound and polymer compound containing the compound
Inventors
Saito, Shohei • Yabu, Hiroshi • Abe, Hiroya
Assignees
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Publication Number
US-12145938-B2
Publication Date
2024-11-19
Expiration Date
Abstract
Provided is a compound having higher fluorescence quantum yield and higher optical stability than a conventional FLAP and a polymer compound containing the compound.A: seven or eight-membered ring structure,Y1, Y2, Y3: halogen atom or the like,a1: number of Y1, a2: number of Y2,B: number of Y3,0≤m and n≤3: when 1≤m≤3, Y1 may be substituted with a structure portion defined by m, when 1≤n≤3, Y2 may be substituted with a structure portion defined by n, andB1, B2: Formulas (2-1) to (2-3):C1, C2, C3: structure containing a cyclic hydrocarbon compound,D1, D2, D3: substructure that inhibits aggregation,E1, E2, E3: polymerizable substructure,Z1: hydrogen atom or the like,c: number of substituent groups Z1,Z2, Z3: hydrogen atom or the like, and may form a ring with C2.
Core Innovation
The invention is directed to a compound represented by a general Formula (1) in which A is represented by general Formula (3) and forms a conjugated system with a benzene ring bound to A. The structure further includes B1 and B2, each represented by general Formula (5-1) having a C=C bond in a 5-member ring as a position to connect to the remainder of general Formula (1), and parameters m and n are integers each independently greater than or equal to 0 and less than or equal to 3.
In general Formula (5-1), D1 denotes a substructure that inhibits aggregation, and E1 denotes a polymerizable substituent group that is any of Formulas (E-1) to (E-19). The substituent group Z1 is selected from a hydrogen atom, a halogen atom, an alkyl group with 1-20 carbons that may have a substituent group, an alkynyl group with 2-20 carbons that may have a substituent group, an aryl group with 6-20 carbons that may have a substituent group, an alkoxy group with 1-10 carbons that may have a substituent group, and a cyano group, and c denotes the number of substituent groups Z1.
The invention also provides polymer compounds formed by polymerizing the general Formula (1) compound. In these polymer compounds, a chemical structure included in the compound can be included in a main chain of the polymer compound, and a cross-linked site can be formed by a chemical structure included in the compound, including a FLAP cross-linkage polyurethane film. The document also describes FLAP compounds and polymer-containing structures intended to improve fluorescence quantum yield and optical stability compared with conventional FLAPs for stress visualization.
Claims Coverage
The consolidated independent claim set includes five inventive features. The claims are directed to a conjugated general Formula (1) compound with benzene-bound A, B1/B2 structures linked through a 5-member ring C=C bond, an aggregation-inhibiting substructure D1 with polymerizable substituent E1, defined Z1 and c, and polymer compounds obtained by polymerizing the Formula (1) compound, including main-chain inclusion of a chemical structure and cross-linked sites.
Conjugated benzene-fused general Formula (1) with ring-linked B1 and B2
A compound represented by general Formula (1) in which A forms a conjugated system with a benzene ring bound to A, and B1 and B2 are each represented by general Formula (5-1) having a C=C bond in a 5-member ring as a position to connect to the remainder of general Formula (1), with m and n each independently greater than or equal to 0 and less than or equal to 3.
Aggregation-inhibiting substructure D1 with polymerizable substituent E1
In general Formula (5-1), D1 denotes a substructure that inhibits aggregation and E1 denotes a polymerizable substituent group that is any of Formulas (E-1) to (E-19).
Defined substituent set Z1 and count c for D1
Z1 is selected from a hydrogen atom, a halogen atom, an alkyl group with 1-20 carbons that may have a substituent group, an alkynyl group with 2-20 carbons that may have a substituent group, an aryl group with 6-20 carbons that may have a substituent group, an alkoxy group with 1-10 carbons that may have a substituent group, and a cyano group, and c denotes the number of substituent groups Z1.
Polymerizing the general Formula (1) compound to form a polymer compound
A polymer compound made by polymerizing a compound represented by general Formula (1).
Main-chain inclusion of a chemical structure in the polymer compound
A polymer compound made by polymerizing a compound represented by general Formula (1), wherein a chemical structure included in the compound is included in a main chain of the polymer compound, and cross-linked sites can be formed by a chemical structure included in the compound.
Together, the independent claims define a conjugated-system compound by general Formula (1) incorporating B1/B2 structures that include a 5-member ring C=C bond, and embed an aggregation-inhibiting substructure D1 bearing a polymerizable substituent E1 selected from Formulas (E-1) to (E-19). The polymer claims cover polymer compounds obtained by polymerizing the Formula (1) compound, including polymer main-chain inclusion of an included chemical structure and cross-linked sites formed by a chemical structure included in the compound.
Stated Advantages
Increased fluorescence quantum yield
Improved optical stability
Improved optical stability with improved retention of fluorescence compared with conventional cyclooctatetraene-condensed anthracene imide dimers.
Improved fluorescence quantum yield and optical stability for sensing-related uses.
Documented Applications
Stress visualization
Viscosity probe and polymers for sensing.
Single-molecule imaging-compatible stability.
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