Aryl substituted propenoic amides and esters
View Patent ↗The present disclosure relates, according to some embodiments, to molecules, including substituted propenoic amides (e.g., aryl substituted propenoic amides), that may receive excited state energy from light-absorbing molecules. According to some embodiments, the present disclosure relates to molecules, including substituted propenoic amides (e.g., aryl substituted propenoic amides), that may quench, dissipate, and/or otherwise resolve excited state energy (e.g., as heat).
1. A composition comprising:
a photoactive molecule; and
a substituted propenoic amide,
wherein the propenoic amide has a structure according to Formula I:
wherein R1 and R1′ are each, independently, a methoxyl group (—OCH 3 ) or a hydrogen (H) with at least one being a methoxyl group (—OCH 3 ),
R2, R2′, R3, R3′, R4, R4′, R5, R5′ are each, independently, H, OH, alkyl, alkoxyl, or a substituted alkyl group,
R6: is cyano or
and
R7 and R8 are each, independently, H, alkyl, substituted alkyl or a polymeric structure, and
wherein the aryl substituted propenoic amide is configured (a) to resolve at least one excited state of the photoactive molecule without observable photochemical reaction, (b) to resolve at least one excited state of the photoactive molecule non-radiatively, or (c) to resolve at least one excited state of the photoactive molecule without observable photochemical reaction and non-radiatively;
wherein the alkyl group may be selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl (2-methylpropyl), t-butyl (1,1-dimethylethyl), and 3,3-dimethylpentane, straight chain hydrocarbon having from about 1 to about 30 (C1-C30) or more carbon atoms, or branched-chain hydrocarbon having from about 1 to about 30 (C1-C30) or more carbon atoms;
wherein the polymeric structure may be selected from polyester, polyamide, polyurethane, polyacrylate, polystyrene, polyolefin, or any copolymer thereof;
wherein the substituted alkyl group may have one or more substituents selected from heteroalkyl, ester, ether, carboxy, cyano, amino, amido, sulfur, halo, or any combination thereof.
2. A composition according to claim 1 , wherein R1 is hydrogen and R1′ is a methoxyl group (—OCH 3 ).
3. A composition according to claim 1 , wherein R1 is a methoxyl group (—OCH 3 ) and R1′ is hydrogen.
4. A composition according to claim 1 , wherein at least one of R2, R2′, R3, R3′, R4, R4′, R5, and R5′ is an alkyl group having from about 1 to about 30 carbon atoms.
5. A composition according to claim 1 , wherein at least one of R2, R2′, R3, R3′, R4, R4′, R5, and R5′ is alkoxyl.
6. A composition according to claim 1 , wherein at least one of R2, R2′, R3, R3′, R4, R4′, R5, and R5′ is a substituted alkyl group;
wherein the substituted alkyl group may have one or more substituents selected from heteroalkyl, ester, ether, carboxy, cyano, amino, amido, sulfur, halo, or any combination thereof.
7. A composition according to claim 1 ,
wherein R6 is
8. A paint, a coating, a cosmetic, a sunscreen, or a pharmaceutical comprising a composition according to claim 1 .
9. A substituted propenoic amide having a structure according to Formula I:
wherein
R1 and R1′ are each, independently, a methoxyl group (—OCH 3 ) or a hydrogen (H) with at least one being a methoxyl group (—OCH 3 ),
R2, R2′, R3, R3′, R4, R4′, R5, R5′ are each, independently, H, OH, alkyl, alkoxyl, or a substituted alkyl group,
R6: is cyano or
and
R7 and R8 are each, independently, H, alkyl, substituted alkyl or a polymeric structure, and
wherein the aryl substituted propenoic amide is configured (a) to resolve at least one excited state of a photoactive molecule without observable photochemical reaction, (b) to resolve at least one excited state of a photoactive molecule non-radiatively, or (c) to resolve at least one excited state of a photoactive molecule without observable photochemical reaction and non-radiatively;
wherein the alkyl group may be selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl (2-methylpropyl), t-butyl (1,1-dimethylethyl), and 3,3-dimethylpentane, straight chain hydrocarbon having from about 1 to about 30 (C1-C30) or more carbon atoms, or branched-chain hydrocarbon having from about 1 to about 30 (C1-C30) or more carbon atoms;
wherein the polymeric structure may be selected from polyester, polyamide, polyurethane, polyacrylate, polystyrene, polyolefin, or any copolymer thereof;
wherein the substituted alkyl group may have one or more substituents selected from heteroalkyl, ester, ether, carboxy, cyano, amino, amido, sulfur, halo, or any combination thereof.
10. A substituted propenoic amide according to claim 9 , wherein R1 is hydrogen and R1′ is a methoxyl group (—OCH 3 ).
11. A substituted propenoic amide according to claim 9 , wherein R1 is a methoxyl group (—OCH 3 ) and R1′ is hydrogen.
12. A substituted propenoic amide according to claim 9 , wherein at least one of R2, R2′, R3, R3′, R4, R4′, R5, and R5′ is an alkyl group having from about 1 to about 30 carbon atoms.
13. A substituted propenoic amide according to claim 9 , wherein at least one of R2, R2′, R3, R3′, R4, R4′, R5, and R5′ is alkoxyl.
14. A substituted propenoic amide according to claim 9 , wherein at least one of R2, R2′, R3, R3′, R4, R4′, R5, and R5′ is a substituted alkyl group;
wherein the substituted alkyl group may have one or more substituents selected from heteroalkyl, ester, ether, carboxy, cyano, amino, amido, sulfur, halo, or any combination thereof.
15. A substituted propenoic amide according to claim 9 ,
wherein R6 is
16. A paint, a coating, a cosmetic, a sunscreen, or a pharmaceutical comprising a substituted propenoic amide according to claim 9 .
17. A method for resolving at least one excited energy state of a photoactive molecule, the method comprising:
positioning the photoactive molecule in electrical communication with a substituted propenoic amide prior to, during, or following excitation of the photoactive molecule to the at least one excited energy state,
wherein the substituted propenoic amide has a structure according to Formula I:
Wherein
R1 and R1′ are each, independently, a methoxyl group (—OCH 3 ) or a hydrogen (H) with at least one being a methoxyl group (—OCH 3 ),
R2, R2′, R3, R3′, R4, R4′, R5, R5′ are each, independently, H, OH, alkyl, alkoxyl, or a substituted alkyl group,
R6: is cyano or
and
R7 and R8 are each, independently, H, alkyl, substituted alkyl or a polymeric structure;
wherein the alkyl group may be selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl (2-methylpropyl), t-butyl (1,1-dimethylethyl), and 3,3-dimethylpentane, straight chain hydrocarbon having from about 1 to about 30 (C1-C30) or more carbon atoms, or branched-chain hydrocarbon having from about 1 to about 30 (C1-C30) or more carbon atoms;
wherein the polymeric structure may be selected from polyester, polyamide, polyurethane, polyacrylate, polystyrene, polyolefin, or any copolymer thereof;
wherein the substituted alkyl group may have one or more substituents selected from heteroalkyl, ester, ether, carboxy, cyano, amino, amido, sulfur, halo, or any combination thereof.
18. A method according to claim 17 , wherein the at least one excited state of the photoactive molecule is resolved without observable photochemical reaction.
19. A method according to claim 17 , wherein the at least one excited state of the photoactive molecule is resolved non-radiatively.
20. A method according to claim 17 , wherein the at least one excited state of the photoactive molecule is resolved without observable photochemical reaction and non-radiatively.