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US5082539A
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Ferrocene compounds and uses thereof
Assignee: Idemitsu Kosan Co Ltd
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Filing: 1990-01-24
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Granted: 1992-01-21
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Expires: 2010-01-24
Abstract
Abstract Novel ferrocene derivatives represented by the general formula: <IMAGE> or the general formula: <IMAGE> or the general formula: <IMAGE> (wherein all the symbols are as described in the specification) are excellent as surfactants. By application of an electrochemical method using the novel ferrocene derivatives or other ferrocene derivatives as a micelle forming agent (surfactant), an organic thin film of a hydrophobic organic substance can be efficiently produced.
Inventors
- 👤 Tetsuo Saji
- 👤 Katsuyoshi Hoshino
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 18:22
CPC Classifications
C; C09; C09K; C09K23/00; C07; C07F; C07F17/00; C07F17/02; C09B; C09B67/00; C09B67/0032; C09B67/0071; C09B67/0084; C09B67/0085; C09D; C09D5/00; C09D5/44; C09D5/448; Y; Y10; Y10S; Y10S516/00; Y10S516/01; Y10S516/02; Y10S516/06; Y10S516/07; Y10S516/905; Y10S516/914; Y10S516/916; Y10S516/917; Y10S516/92
Claims Analysis
Total Claims: 68
Claim 1
Independent Claim
162 words
A ferrocene derivative represented by the general formula: ##STR47## wherein R 1 and R 2 are each independently a hydrogen, a methyl group, an ethyl group, a methoxy group or a carbomethoxy group, R 3 is a hydrogen, a methyl group, an ethyl group, a methoxy group, a carbomethoxy group, a hydroxyl group, carboxyl group or a sulfonic acid group, X is a halogen, and C n H 2n is a straight or branched hydrocarbon group having 4 to 16 carbon atoms; or the general formula: ##STR48## wherein m is an integer of 1 to 4, p is an integer of 1 to 5, r is an integer of 11 to 18, s is a real number of 2.0 to 70, and R 1 and R 2 are the same as described above; or the general formula: ##STR49## wherein w is an integer of 2 to 18, and m, p, s, R 1 and R 2 are the same as described above.
Claim 2
Dependent Claim
162 words
A ferrocene derivative represented by the general formula: ##STR47## wherein R 1 and R 2 are each independently a hydrogen, a methyl group, an ethyl group, a methoxy group or a carbomethoxy group, R 3 is a hydrogen, a methyl group, an ethyl group, a methoxy group, a carbomethoxy group, a hydroxyl group, carboxyl group or a sulfonic acid group, X is a halogen, and C n H 2n is a straight or branched hydrocarbon group having 4 to 16 carbon atoms; or the general formula: ##STR48## wherein m is an integer of 1 to 4, p is an integer of 1 to 5, r is an integer of 11 to 18, s is a real number of 2.0 to 70, and R 1 and R 2 are the same as described above; or the general formula: ##STR49## wherein w is an integer of 2 to 18, and m, p, s, R 1 and R 2 are the same as described above.
Claim 3
Dependent Claim
11 words
The ferrocene derivative according to claim 1 of the formula: ##STR50##
Claim 4
Dependent Claim
26 words
The ferrocene derivative according to claim 1 wherein in formula (I), R 1 , R 2 and R 3 are independently methyl, ethyl or methoxy groups.
Claim 5
Dependent Claim
23 words
The ferrocene derivative according to claim 1 wherein in formula (I), R 3 is a carbomethoxy group, carboxyl group or sulfonic acid group.
Claim 6
Dependent Claim
14 words
The ferrocene derivative according to claim 1 wherein in formula (I) X is Br.
Claim 7
Dependent Claim
43 words
The ferrocene derivative according to claim 1 wherein in formula (I), the group C n H 2n is a tetramethylene group, a pentamethylene group, an octamethylene group, an undecamethylene group, a dodecamethylene group, a hexadecamethylene group, a 2-methylundecamethylene group or a 4-ethylundecamethylene group.
Claim 8
Dependent Claim
27 words
The ferrocene derivative according to claim 1 of the formula: ##STR51## wherein s is a real number from 2 to 50, and r is 11 to 15.
Claim 9
Dependent Claim
11 words
The ferrocene derivative according to claim 7 of the formula: ##STR52##
Claim 10
Dependent Claim
11 words
The ferrocene derivative according to claim 7 of the formula: ##STR53##
Claim 11
Dependent Claim
27 words
The ferrocene derivative according to claim 1 of the formula: ##STR54## wherein s is a real number from 2 to 50 and w is 7 to 15.
Claim 12
Dependent Claim
11 words
The ferrocene derivative according to claim 10 of the formula: ##STR55##
Claim 13
Dependent Claim
11 words
The ferrocene derivative according to claim 10 of the formula: ##STR56##
Claim 14
Dependent Claim
11 words
The ferrocene derivative according to claim 10 of the formula: ##STR57##
Claim 15
Dependent Claim
11 words
The ferrocene derivative according to claim 1 of the formula: ##STR58##
Claim 16
Dependent Claim
11 words
The ferrocene derivative according to claim 1 of the formula: ##STR59##
Claim 17
Dependent Claim
165 words
A surfactant comprising a ferrocene derivative represented by the general formula: ##STR60## wherein R 1 and R 2 are each independently a hydrogen, a methyl group an ethyl group, a methoxy group or a carbomethoxy group, R 3 is a hydrogen, a methyl group, an ethyl group, a methoxy group, a carbomethoxy group, a hydroxyl group, carboxyl group or a sulfonic acid group, X is a halogen, and C n H 2n is a straight or branched hydrocarbon group having 4 to 16 carbon atoms; or the general formula: ##STR61## wherein m is an integer of 1 to 4, p is an integer of 1 to 5, r is an integer of 11 to 18, s is a real number of 2.0 to 70, and R 1 and R 2 are the same as described above, or the general formula: ##STR62## wherein w is an integer of 2 to 18, and m, p, s, R 1 and R 2 are the same as described above.
Claim 18
Dependent Claim
165 words
A surfactant comprising a ferrocene derivative represented by the general formula: ##STR60## wherein R 1 and R 2 are each independently a hydrogen, a methyl group an ethyl group, a methoxy group or a carbomethoxy group, R 3 is a hydrogen, a methyl group, an ethyl group, a methoxy group, a carbomethoxy group, a hydroxyl group, carboxyl group or a sulfonic acid group, X is a halogen, and C n H 2n is a straight or branched hydrocarbon group having 4 to 16 carbon atoms; or the general formula: ##STR61## wherein m is an integer of 1 to 4, p is an integer of 1 to 5, r is an integer of 11 to 18, s is a real number of 2.0 to 70, and R 1 and R 2 are the same as described above, or the general formula: ##STR62## wherein w is an integer of 2 to 18, and m, p, s, R 1 and R 2 are the same as described above.
Claim 19
Dependent Claim
19 words
The surfactant comprising a ferrocene derivative according to claim 16, wherein the ferrocene derivative is of the formula: ##STR63##
Claim 20
Dependent Claim
71 words
The surfactant comprising a ferrocene derivative according to claim 2, wherein in formula (I), R 1 , R 2 and R 3 are independently methyl, ethyl or methoxy groups, R 3 is a carbomethoxy group, a carboxyl group or a sulfonic acid group, X is Br and C n H 2n is a tetramethylene group, a pentamethylene group, an octamethylene group, an undecamethylene group, a dodecamethylene group, or a hexadecamethylene group.
Claim 21
Dependent Claim
29 words
The surfactant comprising a ferrocene derivative according to claim 2, wherein the ferrocene derivative is of the formula: ##STR64## wherein s is a real number from 2 to 50.
Claim 22
Dependent Claim
25 words
The surfactant comprising a ferrocene derivative according to claim 19, wherein the ferrocene derivative is of a formula selected from the group consisting of ##STR65##
Claim 23
Dependent Claim
29 words
The surfactant comprising a ferrocene derivative according to claim 2, wherein the ferrocene derivative is of the formula: ##STR66## wherein s is a real number from 2 to 50.
Claim 24
Dependent Claim
25 words
The surfactant comprising a ferrocene derivative according to claim 21, wherein the ferrocene derivative is of a formula selected from the group consisting of ##STR67##
Claim 25
Dependent Claim
19 words
The surfactant comprising a ferrocene derivative according to claim 16, wherein the ferrocene derivative is of the formula: ##STR68##
Claim 26
Independent Claim
245 words
A method of producing an organic thin film of a hydrophobic substance comprising: forming an aqueous phase of (a) the hydrophobic substance and (c) a ferrocene derivative represented by the general formula: ##STR69## wherein R 1 and R 2 are each independently a hydrogen, a methyl group an ethyl group, a methoxy group or a carbomethoxy group, R 3 is a hydrogen, a methyl group, an ethyl group, a methoxy group, a carbomethoxy group, a hydroxyl group, carboxyl group or a sulfonic acid group, X is a halogen, and C n H 2n is a straight or branched hydrocarbon group having 4 to 16 carbon atoms; or the general formula: ##STR70## wherein m is an integer of 1 to 4, p is an integer of 1 to 5, r is an integer of 11 to 18, s is a real number of 2.0 to 70, and R 1 and R 2 are the same as described above; or the general formula: ##STR71## wherein w is an integer of 2 to 18, and m, p, s, R 1 and R 2 are the same as described above or the general formula: ##STR72## wherein t is an integer of 2 to 10, and R 1 , R 2 , m, p and s are the same as above; providing an electrode in contact with the aqueous phase; and electrolyzing the aqueous phase to form a thin film of the hydrophobic substance on a surface of the electrode.
Claim 27
Independent Claim
245 words
A method of producing an organic thin film of a hydrophobic substance comprising: forming an aqueous phase of (a) the hydrophobic substance and (c) a ferrocene derivative represented by the general formula: ##STR69## wherein R 1 and R 2 are each independently a hydrogen, a methyl group an ethyl group, a methoxy group or a carbomethoxy group, R 3 is a hydrogen, a methyl group, an ethyl group, a methoxy group, a carbomethoxy group, a hydroxyl group, carboxyl group or a sulfonic acid group, X is a halogen, and C n H 2n is a straight or branched hydrocarbon group having 4 to 16 carbon atoms; or the general formula: ##STR70## wherein m is an integer of 1 to 4, p is an integer of 1 to 5, r is an integer of 11 to 18, s is a real number of 2.0 to 70, and R 1 and R 2 are the same as described above; or the general formula: ##STR71## wherein w is an integer of 2 to 18, and m, p, s, R 1 and R 2 are the same as described above or the general formula: ##STR72## wherein t is an integer of 2 to 10, and R 1 , R 2 , m, p and s are the same as above; providing an electrode in contact with the aqueous phase; and electrolyzing the aqueous phase to form a thin film of the hydrophobic substance on a surface of the electrode.
Claim 28
Dependent Claim
42 words
The method according to claim 24, wherein the electrolyzing is conducted at a temperature of the aqueous phase of 0° to 70° C., a voltage of 0.03 to 1.5 V and a current density of not more than 10 mA/cm 2 .
Claim 29
Dependent Claim
17 words
The method according to claim 24 wherein the electrode is of a metal more noble than ferrocene.
Claim 30
Dependent Claim
41 words
The method according to claim 26, wherein the electrode is selected from the group consisting of a mixed oxide of indium oxide and tin oxide, platinum, gold, silver, glassy carbon, an electrically conductive metal oxide, and an electrically conductive organic polymer.
Claim 31
Dependent Claim
41 words
The method according to claim 24, wherein the electrolyzing is conducted at a temperature of the aqueous phase of 20° to 30° C., a voltage of 0.1 to 0.5 V and a current density of 50 to 300 μA/cm 2 .
Claim 32
Independent Claim
248 words
A method of producing an organic thin film of a hydrophobic substance comprising: forming an aqueous phase of (a) the hydrophobic substance, (b) a salt and (c) a ferrocene derivative represented by the general formula: ##STR73## wherein R 1 and R 2 are each independently a hydrogen, a methyl group an ethyl group, a methoxy group or a carbomethoxy group, R 3 is a hydrogen, a methyl group, an ethyl group, a methoxy group, a carbomethoxy group, a hydroxyl group, carboxyl group or a sulfonic acid group, X is a halogen, and C n H 2n is a straight or branched hydrocarbon group having 4 to 16 carbon atoms; or the general formula: ##STR74## wherein m is an integer of 1 to 4, p is an integer of 1 to 5, r is an integer of 11 to 18, s is a real number of 2.0 to 70, and R 1 and R 2 are the same as described above; or the general formula: ##STR75## wherein w is an integer of 2 to 18, and m, p, s, R 1 and R 2 are the same as described above or the general formula: ##STR76## wherein t is an integer of 2 to 10, and R 1 , R 2 , m, p and s are the same as above; providing an electrode in contact with the aqueous phase; and electrolyzing the aqueous phase to form a thin film of the hydrophobic substance on a surface of the electrode.
Claim 33
Independent Claim
248 words
A method of producing an organic thin film of a hydrophobic substance comprising: forming an aqueous phase of (a) the hydrophobic substance, (b) a salt and (c) a ferrocene derivative represented by the general formula: ##STR73## wherein R 1 and R 2 are each independently a hydrogen, a methyl group an ethyl group, a methoxy group or a carbomethoxy group, R 3 is a hydrogen, a methyl group, an ethyl group, a methoxy group, a carbomethoxy group, a hydroxyl group, carboxyl group or a sulfonic acid group, X is a halogen, and C n H 2n is a straight or branched hydrocarbon group having 4 to 16 carbon atoms; or the general formula: ##STR74## wherein m is an integer of 1 to 4, p is an integer of 1 to 5, r is an integer of 11 to 18, s is a real number of 2.0 to 70, and R 1 and R 2 are the same as described above; or the general formula: ##STR75## wherein w is an integer of 2 to 18, and m, p, s, R 1 and R 2 are the same as described above or the general formula: ##STR76## wherein t is an integer of 2 to 10, and R 1 , R 2 , m, p and s are the same as above; providing an electrode in contact with the aqueous phase; and electrolyzing the aqueous phase to form a thin film of the hydrophobic substance on a surface of the electrode.
Claim 34
Dependent Claim
42 words
The method according to claim 29, wherein the electrolyzing is conducted at a temperature of the aqueous phase of 0° to 70° C., a voltage of 0.03 to 1.5 V and a current density of not more than 10 mA/cm 2 .
Claim 35
Dependent Claim
17 words
The method according to claim 29 wherein the electrode is of a metal more noble than ferrocene.
Claim 36
Dependent Claim
25 words
The method according to claim 29, wherein (a), (b) and (c) are dispersed in the aqueous phase by supersonic waves, a homogenizer, or a stirrer.
Claim 37
Dependent Claim
12 words
The method according to claim 32, wherein the salt is lithium sulfate.
Claim 38
Dependent Claim
41 words
The method according to claim 33, wherein the electrolyzing is conducted to a temperature of the aqueous phase of 20° to 30° C., a voltage of 0.1 to 0.5 V and a current density of 50 to 300 μA/cm 2 .
Claim 39
Dependent Claim
22 words
The method according to claim 29, wherein the film formed on the electrode surface comprises particles 600 to 900 Å in size.
Claim 40
Dependent Claim
20 words
The method according to claim 29, further comprising controlling a thickness of the film by controlling current density during electrolyzing.
Claim 41
Dependent Claim
15 words
The method according to claim 29, wherein the ferrocene derivative is of the formula: ##STR77##
Claim 42
Dependent Claim
31 words
The method according to claim 29, wherein the ferrocene derivative is of the formula: ##STR78## wherein s is a real number from 2 to 50 and r is 11 to 15.
Claim 43
Dependent Claim
15 words
The method according to claim 38, wherein the ferrocene derivative is of the formula: ##STR79##
Claim 44
Dependent Claim
31 words
The method according to claim 29, wherein the ferrocene derivative is of the formula: ##STR80## wherein s is a real number from 2 to 50 and w is 7 to 15.
Claim 45
Dependent Claim
21 words
The method according to claim 40, wherein the ferrocene derivative is of a formula selected from the group consisting of ##STR81##
Claim 46
Dependent Claim
21 words
The method according to claim 29, wherein the ferrocene derivative is of a formula selected from the group consisting of ##STR82##
Claim 47
Dependent Claim
20 words
The method according to claim 29, wherein the hydrophobic substance is selected from the group consisting of phthalocyanine and 1-phenylazo-2-naphthol.
Claim 48
Dependent Claim
28 words
The method according to claim 29, wherein the hydrophobic substance is a phthalocyanine complex of a metal selected from the group consisting of iron, zinc, copper and cobalt.
Claim 49
Dependent Claim
58 words
The method according to claim 29, wherein the salt is at least one of a sulfuric acid salt of lithium, potassium, sodium, rubidium, or aluminum or an acetic acid salt of lithium, potassium, sodium, rubidium, aluminum, beryllium, magnesium, strontium or barium and wherein the amount of salt is 10 to 300 times the amount of the ferrocene derivative.
Claim 50
Dependent Claim
32 words
The method according to claim 45, wherein the amount of salt is 50 to 200 times the amount of the ferrocene derivative and wherein the salt is lithium sulfate or lithium bromide.
Claim 51
Independent Claim
223 words
A method of improving the solubility of a hydrophobic substance comprising: forming an aqueous phase of (a) the hydrophobic substance, and (b) a ferrocene derivative represented by the general formula: ##STR83## wherein R 1 and R 2 are each independently a hydrogen, a methyl group an ethyl group, a methoxy group or a carbomethoxy group, R 3 is a hydrogen, a methyl group, an ethyl group, a methoxy group, a carbomethoxy group, a hydroxyl group, carboxyl group or a sulfonic acid group, X is a halogen, and C n H 2n is a straight or branched hydrocarbon group having 4 to 16 carbon atoms; or the general formula: ##STR84## wherein m is an integer of 1 to 4, p is an integer of 1 to 5, r is an integer of 11 to 18, s is a real number of 2.0 to 70, and R 1 and R 2 are the same as described above; or the general formula: ##STR85## wherein w is an integer of 2 to 18, and m, p, s, R 1 and R 2 are the same as described above; or the general formula: ##STR86## wherein t is an integer of 2 to 10, and R 1 , R 2 , m, p and s are the same as above; and dispersing (a) and (b) in the aqueous phase.
Claim 52
Independent Claim
223 words
A method of improving the solubility of a hydrophobic substance comprising: forming an aqueous phase of (a) the hydrophobic substance, and (b) a ferrocene derivative represented by the general formula: ##STR83## wherein R 1 and R 2 are each independently a hydrogen, a methyl group an ethyl group, a methoxy group or a carbomethoxy group, R 3 is a hydrogen, a methyl group, an ethyl group, a methoxy group, a carbomethoxy group, a hydroxyl group, carboxyl group or a sulfonic acid group, X is a halogen, and C n H 2n is a straight or branched hydrocarbon group having 4 to 16 carbon atoms; or the general formula: ##STR84## wherein m is an integer of 1 to 4, p is an integer of 1 to 5, r is an integer of 11 to 18, s is a real number of 2.0 to 70, and R 1 and R 2 are the same as described above; or the general formula: ##STR85## wherein w is an integer of 2 to 18, and m, p, s, R 1 and R 2 are the same as described above; or the general formula: ##STR86## wherein t is an integer of 2 to 10, and R 1 , R 2 , m, p and s are the same as above; and dispersing (a) and (b) in the aqueous phase.
Claim 53
Dependent Claim
41 words
The method according to claim 47, wherein the dispersing is by means of supersonic waves, a homogenizer, or a stirrer, wherein the aqueous phase comprises a salt and wherein the aqueous phase is at a temperature of 0° to 70° C.
Claim 54
Dependent Claim
57 words
The method according to claim 48, wherein the salt is at least one of a sulfuric acid salt of lithium, potassium, sodium, rubidium, or aluminum or an acetic acid of lithium, potassium, sodium, rubidium, aluminum, beryllium, magnesium, strontium or barium and wherein the amount of salt is 10 to 300 times the amount of the ferrocene derivative.
Claim 55
Dependent Claim
32 words
The method according to claim 48, wherein the amount of salt is 50 to 200 times the amount of the ferrocene derivative and wherein the salt is lithium sulfate or lithium bromide.
Claim 56
Dependent Claim
15 words
The method according to claim 47, wherein the ferrocene derivative is of the formula: ##STR87##
Claim 57
Dependent Claim
31 words
The method according to claim 47, wherein the ferrocene derivative is of the formula: ##STR88## wherein s is a real number from 2 to 50 and r is 11 to 15.
Claim 58
Dependent Claim
15 words
The method according to claim 52, wherein the ferrocene derivative is of the formula: ##STR89##
Claim 59
Dependent Claim
31 words
The method according to claim 47, wherein the ferrocene derivative is of the formula: ##STR90## wherein s is a real number from 2 to 50 and w is 7 to 15.
Claim 60
Dependent Claim
21 words
The method according to claim 54, wherein the ferrocene derivative is of a formula selected from the group consisting of ##STR91##
Claim 61
Dependent Claim
21 words
The method according to claim 47, wherein the ferrocene derivative is of a formula selected from the group consisting of ##STR92##
Claim 62
Dependent Claim
20 words
The method according to claim 47, wherein the hydrophobic substance is selected from the group consisting of phthalocyanine and 1-phenyhlazo-2-napthol.
Claim 63
Dependent Claim
28 words
The method according to claim 47, wherein the hydrophobic substance is a phthalocyanine complex of a metal selected from the group consisting of iron, zinc, copper, and cobalt.
Claim 64
Independent Claim
256 words
A method of producing an organic thin film of a hydrophobic substance comprising: forming an aqueous solution of (a) the hydrophobic substance, (b) a salt and (c) a ferrocene derivative of the general formula: ##STR93## wherein R 4 and R 5 are each a hydrogen or an alkyl group having 1 to 4 carbon atoms but not exceeding q as described hereinafter, M and T are each a hydrogen or a substituent, X is a halogen, and q and u are integers satisfying the requirements: q≧0, u≧0, and 4≦q+u≦16; the general formula: ##STR94## wherein R 4 , R 5 , X, M and T are the same as described above provided that the number of carbon atoms of R 4 and R 5 does not exceed h as described hereinafter, and f, h, j and k are integers satisfying the requirements: h≧0, j≧0, k≧1, 0≦f≦k-1 and 3≦h+j+k≦15; the general formula: ##STR95## wherein R 4 , R 5 , X, M and T are the same as described above provided that the number of carbon atoms of R 4 and R 5 does not exceed x as described hereinafter, and x, y and z are integers satisfying the requirements: x≧0, y≧0, z≧1, and 4≦x+y+z≦16; or the general formula: ##STR96## wherein R 4 , R 5 , M, T, x, y and z are the same as described above; providing an electrode in contact with the aqueous phase; and electrolyzing the aqueous phase to form a thin film of the hydrophobic substance on a surface of the electrode.
Claim 65
Independent Claim
256 words
A method of producing an organic thin film of a hydrophobic substance comprising: forming an aqueous solution of (a) the hydrophobic substance, (b) a salt and (c) a ferrocene derivative of the general formula: ##STR93## wherein R 4 and R 5 are each a hydrogen or an alkyl group having 1 to 4 carbon atoms but not exceeding q as described hereinafter, M and T are each a hydrogen or a substituent, X is a halogen, and q and u are integers satisfying the requirements: q≧0, u≧0, and 4≦q+u≦16; the general formula: ##STR94## wherein R 4 , R 5 , X, M and T are the same as described above provided that the number of carbon atoms of R 4 and R 5 does not exceed h as described hereinafter, and f, h, j and k are integers satisfying the requirements: h≧0, j≧0, k≧1, 0≦f≦k-1 and 3≦h+j+k≦15; the general formula: ##STR95## wherein R 4 , R 5 , X, M and T are the same as described above provided that the number of carbon atoms of R 4 and R 5 does not exceed x as described hereinafter, and x, y and z are integers satisfying the requirements: x≧0, y≧0, z≧1, and 4≦x+y+z≦16; or the general formula: ##STR96## wherein R 4 , R 5 , M, T, x, y and z are the same as described above; providing an electrode in contact with the aqueous phase; and electrolyzing the aqueous phase to form a thin film of the hydrophobic substance on a surface of the electrode.
Claim 66
Dependent Claim
21 words
The method according to claim 59, wherein the ferrocene derivative is of the formula selected from the group consisting of ##STR97##
Claim 67
Dependent Claim
39 words
The method according to claim 60, wherein the salt is lithium sulfate, the hydrophobic substance is a copolymer of methacrylate and methacrylic acid and the electrode is an anode of a mixed oxide of indium oxide and tin oxide.
Claim 68
Dependent Claim
33 words
The method according to claim 60, wherein the hydrophobic substance is selected from the group consisting of poly(4-vinylpyridine), phthalocyanine and 1,1'-didodecyl-4,4'-bipyridiniumdibromide and wherein the electrode is an anode of glassy carbon or platinum.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1995-01-20 | 1995-07-22 | 1996-01-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-01-20 | 1999-07-22 | 2000-01-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-01-20 | 2003-07-22 | 2004-01-21 | $7700.00 | Window Closed / Lapsed |