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US 9,701,784 B2Granted
Supramolecular polymers derived from perylene-diimides
AssigneeYeda Research and Development Co. Ltd.
InventorsBoris Rybtchinski, Elijah Shirman, Alona Ustinov, Netanel Ben-Shitrit, Haim Weissman, Elisha M. Krieg, Galina Golubkov, Jonathan Baram
Life of this patent
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Abstract
This invention is directed to perylene-diimide aromatic dianion compounds, process of preparation and uses thereof. The perylene-diimide aromatic dianion compounds of this invention are stable in aqueous solution and can be used for photofunctional and electron transfer systems in aqueous phase. This invention is also directed to supramolecular polymers derived from perylene-diimide compounds and mixtures thereof, and to uses thereof.
Claims29
A compound represented by the structure of formula VIa or VIb:
- wherein
- R1 is [(CH2)nO]oCH3, [(CH2)nC(O)O]oCH3, [(CH2)nC(O)NH]oCH3, [(CH2)nCH2═CH2]oCH3, [(CH2)nCH≡CH]oCH3, [(CH2)nNH]oCH3, linear or branched (C1-C32)alkyl, (C3-C8)cycloalkyl, aryl, heteroaryl, (C1-C32)alkyl-COOH, (C1-C32)alkyl-Si-A, or [C(O)CHR3NH]pH wherein said aryl or heteroaryl groups are optionally substituted by 1-3 substituents selected from halide, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
- wherein A comprises three same or different of the following substituents Cl, Br, I, O(C1-C8)alkyl or (C1-C8)alkyl;
- and wherein R3 in said [C(O)CHR3NH]pH is independently the same or different H, (C1-C6)alkyl, (C1-C6)hydroxyalkyl, (C1-C6)mercaptoalkyl, (C1-C6)aminoalkyl, (C1-C6)carboxyalkyl, (C1-C6)carboxamidoalkyl, (C1-C6)guanidinoalkyl, aryl, (aryl)alkyl, heteroaryl or (heteroaryl)alkyl;
- R2 is [(CH2)qO]rCH3, [(CH2)qC(O)O]rCH3, [(CH2)qC(O)NH]rCH3, [(CH2)qCH2═CH2]rCH3, [(CH2)qCH≡CH]rCH3, [(CH2)qNH]rCH3, linear or branched (C1-C32)alkyl, (C3-C8)cycloalkyl, aryl, heteroaryl, (C1-C32)alkyl-COOH, (C1-C32)alkyl-Si-A, or [C(O)CHR4NH]sH wherein said aryl or heteroaryl groups are optionally substituted by substituents selected from halide, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
- wherein A comprises three same or different of the following substituents Cl, Br, I, O(C1-C8)alkyl or (C1-C8)alkyl;
- and wherein R4 in said [C(O)CHR4NH]sH is independently the same or different H, (C1-C6)alkyl, (C1-C6)hydroxyalkyl, (C1-C6)mercaptoalkyl, (C1-C6)aminoalkyl, (C1-C6)carboxyalkyl, (C1-C6)carboxamidoalkyl, (C1-C6)guanidinoalkyl, aryl, (aryl)alkyl, heteroaryl or (heteroaryl)alkyl;
- R5 is —ORx where Rx is C1-C6 alkyl or [(CH2)nO]oCH3, aryl, heteroaryl, C≡C—R7, CH═CR8R9, NR10R11 or a saturated carbocyclic or heterocyclic ring wherein said saturated heterocyclic ring or heteroaryl contains at least one nitrogen atom and R5 is connected via the nitrogen atom and wherein said saturated carbocyclic ring, heterocyclic ring, aryl and heteroaryl groups are optionally substituted by 1-3 substituents selected from halide, aryl, heteroaryl, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
- R7 is H, halo, (C1-C32)alkyl, aryl, heteroaryl, Si(H)3 or Si[(C1-C8)alkyl]3 wherein said aryl or heteroaryl groups are optionally substituted by 1-3 substituents selected from halide, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
- R8, R9, R10 and R11 are independently H, (C1-C32)alkyl, aryl or heteroaryl wherein said aryl or heteroaryl groups are optionally substituted by 1-3 substituents selected from halide, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
- L is an ethynyl group or a diethynylbenzene group;
- P is a perylene-diimide group represented by the structure of formula Va or Vb:
- n is an integer from 1-5;
- o is an integer from 1-100;
- p is an integer from 1-100;
- q is an integer from 2-5;
- r is an integer from 1-100;
- and
- s is an integer from 1-100;
- or a metal complex thereof.
17 more elements
A compound represented by the structure of formula VIa or VIb:
- wherein
- R1 is [(CH2)nO]oCH3, [(CH2)nC(O)O]oCH3, [(CH2)nC(O)NH]oCH3, [(CH2)nCH2═CH2]oCH3, [(CH2)nCH≡CH]oCH3, [(CH2)nNH]oCH3, linear or branched (C1-C32)alkyl, (C3-C8)cycloalkyl, aryl, heteroaryl, (C1-C32)alkyl-COOH, (C1-C32)alkyl-Si-A, or [C(O)CHR3NH]pH wherein said aryl or heteroaryl groups are optionally substituted by 1-3 substituents selected from halide, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
- wherein A comprises three same or different of the following substituents Cl, Br, I, O(C1-C8)alkyl or (C1-C8)alkyl;
- and wherein R3 in said [C(O)CHR3NH]pH is independently the same or different H, (C1-C6)alkyl, (C1-C6)hydroxyalkyl, (C1-C6)mercaptoalkyl, (C1-C6)aminoalkyl, (C1-C6)carboxyalkyl, (C1-C6)carboxamidoalkyl, (C1-C6)guanidinoalkyl, aryl, (aryl)alkyl, heteroaryl or (heteroaryl)alkyl;
- R2 is [(CH2)qO]rCH3, [(CH2)qC(O)O]rCH3, [(CH2)qC(O)NH]rCH3, [(CH2)qCH2═CH2]rCH3, [(CH2)qCH≡CH]rCH3, [(CH2)qNH]rCH3, linear or branched (C1-C32)alkyl, (C3-C8)cycloalkyl, aryl, heteroaryl, (C1-C32)alkyl-COOH, (C1-C32)alkyl-Si-A, or [C(O)CHR4NH]sH wherein said aryl or heteroaryl groups are optionally substituted by substituents selected from halide, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
- wherein A comprises three same or different of the following substituents Cl, Br, I, O(C1-C8)alkyl or (C1-C8)alkyl;
- and wherein R4 in said [C(O)CHR4NH]sH is independently the same or different H, (C1-C6)alkyl, (C1-C6)hydroxyalkyl, (C1-C6)mercaptoalkyl, (C1-C6)aminoalkyl, (C1-C6)carboxyalkyl, (C1-C6)carboxamidoalkyl, (C1-C6)guanidinoalkyl, aryl, (aryl)alkyl, heteroaryl or (heteroaryl)alkyl;
- R5 is —ORx where Rx is C1-C6 alkyl or [(CH2)nO]oCH3, aryl, heteroaryl, C≡C—R7, CH═CR8R9, NR10R11 or a saturated carbocyclic or heterocyclic ring wherein said saturated heterocyclic ring or heteroaryl contains at least one nitrogen atom and R5 is connected via the nitrogen atom and wherein said saturated carbocyclic ring, heterocyclic ring, aryl and heteroaryl groups are optionally substituted by 1-3 substituents selected from halide, aryl, heteroaryl, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
- R7 is H, halo, (C1-C32)alkyl, aryl, heteroaryl, Si(H)3 or Si[(C1-C8)alkyl]3 wherein said aryl or heteroaryl groups are optionally substituted by 1-3 substituents selected from halide, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
- R8, R9, R10 and R11 are independently H, (C1-C32)alkyl, aryl or heteroaryl wherein said aryl or heteroaryl groups are optionally substituted by 1-3 substituents selected from halide, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
- L is a diethynyldipyridine group;
- P is a perylene-diimide group represented by the structure of formula Va or Vb:
- n is an integer from 1-5;
- o is an integer from 1-100;
- p is an integer from 1-100;
- q is an integer from 2-5;
- r is an integer from 1-100;
- and
- s is an integer from 1-100;
- or a metal complex thereof.
17 more elements
Dependencies are inferred from the claim text.