In situ patterning of electrolyte for molecular information storage devices
First Claim
1. A method of patterning an electrolyte on a surface, said method comprising:
- i) contacting said surface with a compound having the formula;
R-L2-M-L1-Z1whereinZ1 is a surface attachment group;
L1 and L2 are independently selected linkers or covalent bonds;
M is an information storage molecule comprising a redox active moiety; and
R is a protected or unprotected reactive site or group;
whereby said contacting is under conditions that result in attachment of said redox-active moiety to said surface via said surface attachment group; and
ii) contacting the surface-attached redox-active moiety with an electrolyte having the formula;
J-QwhereinJ is a charged moiety; and
Q is a reactive group that is reactive with said reactive group (R) under conditions that result in the covalent attachment of said charged moiety (J) to said information storage molecule thereby patterning said electrolyte on said surface.
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Accused Products
Abstract
This invention pertains to methods assembly of organic molecules and electrolytes in hybrid electronic. In one embodiment, a method is provided that involves contacting a surface/electrode with a compound of formula: R-L2-M-L1-Z1 where Z1 is a surface attachment group; L1 and L2 are independently linker or covalent bonds; M is an information storage molecule; and R is a protected or unprotected reactive site or group; where the contacting results in attachment of the redox-active moiety to the surface via the surface attachment group; and ii) contacting the surface-attached information storage molecule with an electrolyte having the formula: J-Q where J is a charged moiety (e.g., an electrolyte); and Q is a reactive group that is reactive with the reactive group (R) and attaches J to the information storage molecule thereby patterning the electrolyte on the surface.
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Citations
30 Claims
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1. A method of patterning an electrolyte on a surface, said method comprising:
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i) contacting said surface with a compound having the formula;
R-L2-M-L1-Z1wherein Z1 is a surface attachment group; L1 and L2 are independently selected linkers or covalent bonds; M is an information storage molecule comprising a redox active moiety; and R is a protected or unprotected reactive site or group; whereby said contacting is under conditions that result in attachment of said redox-active moiety to said surface via said surface attachment group; and ii) contacting the surface-attached redox-active moiety with an electrolyte having the formula;
J-Qwherein J is a charged moiety; and Q is a reactive group that is reactive with said reactive group (R) under conditions that result in the covalent attachment of said charged moiety (J) to said information storage molecule thereby patterning said electrolyte on said surface. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30)
4-aminophenyl, 2-(4-aminophenyl)ethynyl, 4-[2-(4-aminophenyl)ethynyl]phenyl, 4-aminobiphenyl, 1,1,1-tris[4-(S-acetylthiomethyl)phenyl]methyl, 4-{1,1,1-tris[4-(S-acetylthiomethyl)phenyl]methyl}phenyl, 1,1,1-tris[4-(dihydroxyphosphoryl)phenyl]methyl, 4-{1,1,1-tris[4-(dihydroxyphosphoryl)phenyl]methyl}phenyl, 1,1,1-tris[4-(dihydroxyphosphorylmethyl)phenyl]methyl, and 4-{1,1,1-tris[4-(dihydroxyphosphorylmethyl)phenyl]methyl}phenyl.
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12. The method of claim 1, wherein L1 and L2 are independently selected from the group consisting of a covalent bond, 1,4-phenylene, 4,4′
- -diphenylethyne, 4,4′
-diphenylbutadiyne, 4,4′
-biphenyl, 4,4′
-stilbene, 1,4-bicyclooctane, 4,4′
-azobenzene, 4,4′
-benzylideneaniline, and 4,4″
-terphenyl.
- -diphenylethyne, 4,4′
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13. The method of claim 1, wherein said electrolyte bearing a reactive site (Q) is selected from the group consisting of an acyl hydrazide, an amine, a dipyrrin, acac, a phenol, an alcohol, a diol, a thiol, an azide, a phenanthroline, alkyl, halide, aldehyde, a zirconium dichloride, and a zirconium hydroxide.
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14. The method of claim 1, wherein R is selected from the group consisting of a carboxaldehyde, a ketone, an o-hydroxycarboxaldehyde, a dipyrrin, an amine, and acac.
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15. The method of claim 1, wherein R is a carboxaldehyde or ketone and Q is an acylhydrazide.
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16. The method of claim 1, wherein R is a carboxaldehyde or ketone and Q is an amine.
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17. The method of claim 1, wherein R is an o-hydroxycarboxaldehyde and Q is an amine.
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18. The method of claim 1, wherein R is an o-hydroxycarboxaldehyde and Q is an acyl hydrazide.
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19. The method of claim 1, wherein R is a dipyrrin and Q is a dipyrrin.
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20. The method of claim 1, wherein R is acac and Q is acac.
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21. The method of claim 1, further comprising contacting said charged moiety with a reagent having formula
Z2-L3-K Ywherein K comprises a group having a charge complementary to the charge of J; -
L3 is a covalent bond or a linker; Z2 is a surface attachment group; and Y is a counterion; whereby K electrostatically associates with J thereby providing a counterion group associated with said information storage molecule where said counterion group comprises said surface attachment group Z2.
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22. The method of claim 21, further comprising constructing a counter-electrode by binding an electrode to said surface attachment group Z2.
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23. The method of claim 22, wherein said electrode comprises a conductive material.
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24. The method of claim 22, wherein said electrode comprises a semiconductive material.
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25. The method of claim 21, wherein Z2 is a protected or unprotected reactive site or group selected from the group consisting of a carboxylic acid, an alcohol, a thiol, a selenol, a tellurol, a phosphonic acid, a phosphonothioate, an amine, and a nitrile.
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26. The method of claim 21, wherein -L3-Z2 is selected from the group consisting of:
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4-carboxyphenyl, 2-(4-carboxyphenyl)ethynyl, 4-(2-(4-carboxyphenyl)ethynyl)phenyl, 4-carboxymethylphenyl, 4-(3-carboxypropyl)phenyl, 4-(2-(4-carboxymethylphenyl)ethynyl) phenyl, 4-hydroxyphenyl, 2-(4-hydroxyphenyl)ethynyl, 4-(2-(4-hydroxyphenyl)ethynyl)phenyl, 4-hydroxymethylphenyl, 4-(2-hydroxyethyl)phenyl, 4-(3-hydroxypropyl)phenyl, 4-(2-(4-hydroxymethylphenyl)ethynyl)phenyl, 4-mercaptophenyl, 2-(4-mercaptophenyl)ethynyl, 4-(2-(4-mercaptophenyl)ethynyl)phenyl, 4-mercaptomethylphenyl, 4-(2-mercaptoethyl)phenyl, 4-(3-mercaptopropyl)phenyl, 4-(2-(4-mercaptomethylphenyl)ethynyl)phenyl, 4-selenylphenyl, 2-(4-selenylphenyl)ethynyl, 4-selenylmethylphenyl, 4-(2-selenylethyl)phenyl, 4-(3-selenylpropyl)phenyl, 4-selenylmethylphenyl, 4-(2-(4-selenylphenyl)ethynyl)phenyl, 4-tellurylphenyl, 2-(4-tellurylphenyl)ethynyl, 4-(2-(4-tellurylphenyl)ethynyl)phenyl, 4-tellurylmethylphenyl, 4-(2-tellurylethyl)phenyl, 4-(3-tellurylpropyl)phenyl, 4-(2-(4-tellurylmethylphenyl)ethynyl)phenyl, 4-(dihydroxyphosphoryl)phenyl, 2-[4-(dihydroxyphosphoryl)phenyl]ethynyl, 4-[2-[4-(dihydroxyphosphoryl)phenyl]ethynyl]phenyl, 4-[(dihydroxyphosphoryl)methyl]phenyl, 4-[2-(dihydroxyphosphoryl)ethyl]phenyl, 4-[2-[4-(dihydroxyphosphoryl)methylphenyl]ethynyl]phenyl, 4-(hydroxy(mercapto)phosphoryl)phenyl, 2-[4-(hydroxy(mercapto)phosphoryl)phenyl]ethynyl, 4-[2-[4-(hydroxy(mercapto)phosphoryl)phenyl]ethynyl]phenyl, 4-[(hydroxy(mercapto)phosphoryl)methyl]phenyl, 4-[2-(hydroxy(mercapto)phosphoryl)ethyl]phenyl, 4-[2-[4-(hydroxy(mercapto)phosphoryl)methylphenyl]ethynyl]phenyl, 4-cyanophenyl, 2-(4-cyanophenyl)ethynyl, 4-[2-(4-cyanophenyl)ethynyl]phenyl, 4-(cyanomethyl)phenyl, 4-(2-cyanoethyl)phenyl, 4-[2-[4-(cyanomethyl)phenyl]ethynyl]phenyl;
4-cyanobiphenyl,4-aminophenyl, 2-(4-aminophenyl)ethynyl, 4-[2-(4-aminophenyl)ethynyl]phenyl, 4-aminobiphenyl, 1,1,1-tris[4-(S-acetylthiomethyl)phenyl]methyl, 4-{1,1,1-tris[4-(S-acetylthiomethyl)phenyl]methyl}phenyl, 1,1,1-tris[4-(dihydroxyphosphoryl)phenyl]methyl, 4-{1,1,1-tris[4-(dihydroxyphosphoryl)phenyl]methyl}phenyl, 1,1,1-tris[4-(dihydroxyphosphorylmethyl)phenyl]methyl, and 4-{1,1,1-tris[4-(dihydroxyphosphorylmethyl)phenyl]methyl}phenyl.
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27. The method of claim 21, wherein L3 is selected from the group consisting of a covalent bond, 1,4-phenylene, 4,4′
- -diphenylethyne, 4,4′
-diphenylbutadiyne, 4,4′
-biphenyl, 4,4′
-stilbene, 1,4-bicyclooctane, 4,4′
-azobenzene, 4,4′
-benzylideneaniline, and 4,4″
-terphenyl.
- -diphenylethyne, 4,4′
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28. The method of claim 21, wherein the counterion (K) is selected from the group consisting of a halogen, an alkali earth metal, PF6, and ClO4.
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29. The method of claim 21, wherein Z2-L3-K-Y+ is selected from the group consisting of 11-mercaptoundecanoic acid, 16-mercaptohexadecanoic acid, 3-mercapto-1-propanoic acid, (2-mercaptoethyl)trimethylammonium bromide, and 4-(mercaptomethyl)benzenesulfonic acid.
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30. The method of claim 21, wherein said counterion is altered by an ion-exchange process.
Specification