Doping of conducting polymers by sulfonated fullerene derivatives and dendrimers

Journal of Physical Chemistry B

Volumn 102, Issue 21, 1998, Pages 4049-4053

  Dai, Liming ^a   Lu, Jianping ^a,b   Matthews, Barry ^a   Mau, Albert W H ^a  

^a CSIRO   (Australia)

^b TSINGHUA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001497724     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp980410y     Document Type: Article

References (77)

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42. See, for example: (a) MacDiarmid, A. G. Synth. Met. 1997, 84, 27. (b) Yang, Y.; Heeger, A. J. Appl. Phys. Lett. 1994, 64, 1245. (c) Reiss, H.; Kaner, R. B.; Anderson, M. R.; Matts, B. R. Science 1991, 252, 1412. (d) Gong, X.; Dai, L.; Mau, A. W. H.; Griesser, H. J. J. Polym. Sci., Part A: Polym. Chem., in press and references therein. (e) MacDiamid, A. G.; Chiang, J. C.; Richterm, A. F.; Somasiri, N. L. D.; Epstein, A. J. In Conducting Polymers: Special Applications; Alcácer, L., Ed.; D. Reidel Publishing Co.: Dordrecht, 1986. (f) MacDiarmid, A. G.; Epstein, A. J. Synth. Met. 1994, 65, 103; 1995, 69, 85. (g) Xia, Y.; Wiesinger, J. M.; MacDiarmid, A. G.; Epstein, A. J. Chem. Mater. 1995, 7, 443. (h) Cheng, S.-A.; Lin, L. C. Macromolecules 1995, 28, 1239 and references therein. (i) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Appl. Phys. Lett. 1992, 60, 2711. (j) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Synth. Met. 1992, 48, 91.
43. See, for example: (a) MacDiarmid, A. G. Synth. Met. 1997, 84, 27. (b) Yang, Y.; Heeger, A. J. Appl. Phys. Lett. 1994, 64, 1245. (c) Reiss, H.; Kaner, R. B.; Anderson, M. R.; Matts, B. R. Science 1991, 252, 1412. (d) Gong, X.; Dai, L.; Mau, A. W. H.; Griesser, H. J. J. Polym. Sci., Part A: Polym. Chem., in press and references therein. (e) MacDiamid, A. G.; Chiang, J. C.; Richterm, A. F.; Somasiri, N. L. D.; Epstein, A. J. In Conducting Polymers: Special Applications; Alcácer, L., Ed.; D. Reidel Publishing Co.: Dordrecht, 1986. (f) MacDiarmid, A. G.; Epstein, A. J. Synth. Met. 1994, 65, 103; 1995, 69, 85. (g) Xia, Y.; Wiesinger, J. M.; MacDiarmid, A. G.; Epstein, A. J. Chem. Mater. 1995, 7, 443. (h) Cheng, S.-A.; Lin, L. C. Macromolecules 1995, 28, 1239 and references therein. (i) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Appl. Phys. Lett. 1992, 60, 2711. (j) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Synth. Met. 1992, 48, 91.
44. See, for example: (a) MacDiarmid, A. G. Synth. Met. 1997, 84, 27. (b) Yang, Y.; Heeger, A. J. Appl. Phys. Lett. 1994, 64, 1245. (c) Reiss, H.; Kaner, R. B.; Anderson, M. R.; Matts, B. R. Science 1991, 252, 1412. (d) Gong, X.; Dai, L.; Mau, A. W. H.; Griesser, H. J. J. Polym. Sci., Part A: Polym. Chem., in press and references therein. (e) MacDiamid, A. G.; Chiang, J. C.; Richterm, A. F.; Somasiri, N. L. D.; Epstein, A. J. In Conducting Polymers: Special Applications; Alcácer, L., Ed.; D. Reidel Publishing Co.: Dordrecht, 1986. (f) MacDiarmid, A. G.; Epstein, A. J. Synth. Met. 1994, 65, 103; 1995, 69, 85. (g) Xia, Y.; Wiesinger, J. M.; MacDiarmid, A. G.; Epstein, A. J. Chem. Mater. 1995, 7, 443. (h) Cheng, S.-A.; Lin, L. C. Macromolecules 1995, 28, 1239 and references therein. (i) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Appl. Phys. Lett. 1992, 60, 2711. (j) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Synth. Met. 1992, 48, 91.
45. See, for example: (a) MacDiarmid, A. G. Synth. Met. 1997, 84, 27. (b) Yang, Y.; Heeger, A. J. Appl. Phys. Lett. 1994, 64, 1245. (c) Reiss, H.; Kaner, R. B.; Anderson, M. R.; Matts, B. R. Science 1991, 252, 1412. (d) Gong, X.; Dai, L.; Mau, A. W. H.; Griesser, H. J. J. Polym. Sci., Part A: Polym. Chem., in press and references therein. (e) MacDiamid, A. G.; Chiang, J. C.; Richterm, A. F.; Somasiri, N. L. D.; Epstein, A. J. In Conducting Polymers: Special Applications; Alcácer, L., Ed.; D. Reidel Publishing Co.: Dordrecht, 1986. (f) MacDiarmid, A. G.; Epstein, A. J. Synth. Met. 1994, 65, 103; 1995, 69, 85. (g) Xia, Y.; Wiesinger, J. M.; MacDiarmid, A. G.; Epstein, A. J. Chem. Mater. 1995, 7, 443. (h) Cheng, S.-A.; Lin, L. C. Macromolecules 1995, 28, 1239 and references therein. (i) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Appl. Phys. Lett. 1992, 60, 2711. (j) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Synth. Met. 1992, 48, 91.
46. See, for example: (a) MacDiarmid, A. G. Synth. Met. 1997, 84, 27. (b) Yang, Y.; Heeger, A. J. Appl. Phys. Lett. 1994, 64, 1245. (c) Reiss, H.; Kaner, R. B.; Anderson, M. R.; Matts, B. R. Science 1991, 252, 1412. (d) Gong, X.; Dai, L.; Mau, A. W. H.; Griesser, H. J. J. Polym. Sci., Part A: Polym. Chem., in press and references therein. (e) MacDiamid, A. G.; Chiang, J. C.; Richterm, A. F.; Somasiri, N. L. D.; Epstein, A. J. In Conducting Polymers: Special Applications; Alcácer, L., Ed.; D. Reidel Publishing Co.: Dordrecht, 1986. (f) MacDiarmid, A. G.; Epstein, A. J. Synth. Met. 1994, 65, 103; 1995, 69, 85. (g) Xia, Y.; Wiesinger, J. M.; MacDiarmid, A. G.; Epstein, A. J. Chem. Mater. 1995, 7, 443. (h) Cheng, S.-A.; Lin, L. C. Macromolecules 1995, 28, 1239 and references therein. (i) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Appl. Phys. Lett. 1992, 60, 2711. (j) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Synth. Met. 1992, 48, 91.
47. See, for example: (a) MacDiarmid, A. G. Synth. Met. 1997, 84, 27. (b) Yang, Y.; Heeger, A. J. Appl. Phys. Lett. 1994, 64, 1245. (c) Reiss, H.; Kaner, R. B.; Anderson, M. R.; Matts, B. R. Science 1991, 252, 1412. (d) Gong, X.; Dai, L.; Mau, A. W. H.; Griesser, H. J. J. Polym. Sci., Part A: Polym. Chem., in press and references therein. (e) MacDiamid, A. G.; Chiang, J. C.; Richterm, A. F.; Somasiri, N. L. D.; Epstein, A. J. In Conducting Polymers: Special Applications; Alcácer, L., Ed.; D. Reidel Publishing Co.: Dordrecht, 1986. (f) MacDiarmid, A. G.; Epstein, A. J. Synth. Met. 1994, 65, 103; 1995, 69, 85. (g) Xia, Y.; Wiesinger, J. M.; MacDiarmid, A. G.; Epstein, A. J. Chem. Mater. 1995, 7, 443. (h) Cheng, S.-A.; Lin, L. C. Macromolecules 1995, 28, 1239 and references therein. (i) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Appl. Phys. Lett. 1992, 60, 2711. (j) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Synth. Met. 1992, 48, 91.
48. See, for example: (a) MacDiarmid, A. G. Synth. Met. 1997, 84, 27. (b) Yang, Y.; Heeger, A. J. Appl. Phys. Lett. 1994, 64, 1245. (c) Reiss, H.; Kaner, R. B.; Anderson, M. R.; Matts, B. R. Science 1991, 252, 1412. (d) Gong, X.; Dai, L.; Mau, A. W. H.; Griesser, H. J. J. Polym. Sci., Part A: Polym. Chem., in press and references therein. (e) MacDiamid, A. G.; Chiang, J. C.; Richterm, A. F.; Somasiri, N. L. D.; Epstein, A. J. In Conducting Polymers: Special Applications; Alcácer, L., Ed.; D. Reidel Publishing Co.: Dordrecht, 1986. (f) MacDiarmid, A. G.; Epstein, A. J. Synth. Met. 1994, 65, 103; 1995, 69, 85. (g) Xia, Y.; Wiesinger, J. M.; MacDiarmid, A. G.; Epstein, A. J. Chem. Mater. 1995, 7, 443. (h) Cheng, S.-A.; Lin, L. C. Macromolecules 1995, 28, 1239 and references therein. (i) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Appl. Phys. Lett. 1992, 60, 2711. (j) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Synth. Met. 1992, 48, 91.
49. See, for example: (a) MacDiarmid, A. G. Synth. Met. 1997, 84, 27. (b) Yang, Y.; Heeger, A. J. Appl. Phys. Lett. 1994, 64, 1245. (c) Reiss, H.; Kaner, R. B.; Anderson, M. R.; Matts, B. R. Science 1991, 252, 1412. (d) Gong, X.; Dai, L.; Mau, A. W. H.; Griesser, H. J. J. Polym. Sci., Part A: Polym. Chem., in press and references therein. (e) MacDiamid, A. G.; Chiang, J. C.; Richterm, A. F.; Somasiri, N. L. D.; Epstein, A. J. In Conducting Polymers: Special Applications; Alcácer, L., Ed.; D. Reidel Publishing Co.: Dordrecht, 1986. (f) MacDiarmid, A. G.; Epstein, A. J. Synth. Met. 1994, 65, 103; 1995, 69, 85. (g) Xia, Y.; Wiesinger, J. M.; MacDiarmid, A. G.; Epstein, A. J. Chem. Mater. 1995, 7, 443. (h) Cheng, S.-A.; Lin, L. C. Macromolecules 1995, 28, 1239 and references therein. (i) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Appl. Phys. Lett. 1992, 60, 2711. (j) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Synth. Met. 1992, 48, 91.
50. See, for example: (a) MacDiarmid, A. G. Synth. Met. 1997, 84, 27. (b) Yang, Y.; Heeger, A. J. Appl. Phys. Lett. 1994, 64, 1245. (c) Reiss, H.; Kaner, R. B.; Anderson, M. R.; Matts, B. R. Science 1991, 252, 1412. (d) Gong, X.; Dai, L.; Mau, A. W. H.; Griesser, H. J. J. Polym. Sci., Part A: Polym. Chem., in press and references therein. (e) MacDiamid, A. G.; Chiang, J. C.; Richterm, A. F.; Somasiri, N. L. D.; Epstein, A. J. In Conducting Polymers: Special Applications; Alcácer, L., Ed.; D. Reidel Publishing Co.: Dordrecht, 1986. (f) MacDiarmid, A. G.; Epstein, A. J. Synth. Met. 1994, 65, 103; 1995, 69, 85. (g) Xia, Y.; Wiesinger, J. M.; MacDiarmid, A. G.; Epstein, A. J. Chem. Mater. 1995, 7, 443. (h) Cheng, S.-A.; Lin, L. C. Macromolecules 1995, 28, 1239 and references therein. (i) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Appl. Phys. Lett. 1992, 60, 2711. (j) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Synth. Met. 1992, 48, 91.
51. See, for example: (a) MacDiarmid, A. G. Synth. Met. 1997, 84, 27. (b) Yang, Y.; Heeger, A. J. Appl. Phys. Lett. 1994, 64, 1245. (c) Reiss, H.; Kaner, R. B.; Anderson, M. R.; Matts, B. R. Science 1991, 252, 1412. (d) Gong, X.; Dai, L.; Mau, A. W. H.; Griesser, H. J. J. Polym. Sci., Part A: Polym. Chem., in press and references therein. (e) MacDiamid, A. G.; Chiang, J. C.; Richterm, A. F.; Somasiri, N. L. D.; Epstein, A. J. In Conducting Polymers: Special Applications; Alcácer, L., Ed.; D. Reidel Publishing Co.: Dordrecht, 1986. (f) MacDiarmid, A. G.; Epstein, A. J. Synth. Met. 1994, 65, 103; 1995, 69, 85. (g) Xia, Y.; Wiesinger, J. M.; MacDiarmid, A. G.; Epstein, A. J. Chem. Mater. 1995, 7, 443. (h) Cheng, S.-A.; Lin, L. C. Macromolecules 1995, 28, 1239 and references therein. (i) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Appl. Phys. Lett. 1992, 60, 2711. (j) Cao, Y.; Treacy, G. M.; Smith, P.; Heeger, A. J. Synth. Met. 1992, 48, 91.
52. See, for example: (a) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H. B.; Jaworek, W.; Vogue, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Tomalia, D. A.; Durst, H. D. Top. Curr. Chem. 1993, 165, 193. (d) Tomalia, D. A. Adv. Mater. 1994, 6, 529. (e) Issberner, J.; Moors, R.; Vogtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (f) Newlome, G. R.; Moorefield, C. N.; Baker, G. R. Aldrichimica Acta 1992, 25, 31. (g) Service, R. F. Science 1995, 267, 458. (h) Matthews, B. R.; Holan, G. Int. Pat. Appl. WO 95/34595, Dec 21, 1995.
53. See, for example: (a) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H. B.; Jaworek, W.; Vogue, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Tomalia, D. A.; Durst, H. D. Top. Curr. Chem. 1993, 165, 193. (d) Tomalia, D. A. Adv. Mater. 1994, 6, 529. (e) Issberner, J.; Moors, R.; Vogtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (f) Newlome, G. R.; Moorefield, C. N.; Baker, G. R. Aldrichimica Acta 1992, 25, 31. (g) Service, R. F. Science 1995, 267, 458. (h) Matthews, B. R.; Holan, G. Int. Pat. Appl. WO 95/34595, Dec 21, 1995.
54. See, for example: (a) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H. B.; Jaworek, W.; Vogue, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Tomalia, D. A.; Durst, H. D. Top. Curr. Chem. 1993, 165, 193. (d) Tomalia, D. A. Adv. Mater. 1994, 6, 529. (e) Issberner, J.; Moors, R.; Vogtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (f) Newlome, G. R.; Moorefield, C. N.; Baker, G. R. Aldrichimica Acta 1992, 25, 31. (g) Service, R. F. Science 1995, 267, 458. (h) Matthews, B. R.; Holan, G. Int. Pat. Appl. WO 95/34595, Dec 21, 1995.
55. See, for example: (a) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H. B.; Jaworek, W.; Vogue, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Tomalia, D. A.; Durst, H. D. Top. Curr. Chem. 1993, 165, 193. (d) Tomalia, D. A. Adv. Mater. 1994, 6, 529. (e) Issberner, J.; Moors, R.; Vogtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (f) Newlome, G. R.; Moorefield, C. N.; Baker, G. R. Aldrichimica Acta 1992, 25, 31. (g) Service, R. F. Science 1995, 267, 458. (h) Matthews, B. R.; Holan, G. Int. Pat. Appl. WO 95/34595, Dec 21, 1995.
56. See, for example: (a) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H. B.; Jaworek, W.; Vogue, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Tomalia, D. A.; Durst, H. D. Top. Curr. Chem. 1993, 165, 193. (d) Tomalia, D. A. Adv. Mater. 1994, 6, 529. (e) Issberner, J.; Moors, R.; Vogtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (f) Newlome, G. R.; Moorefield, C. N.; Baker, G. R. Aldrichimica Acta 1992, 25, 31. (g) Service, R. F. Science 1995, 267, 458. (h) Matthews, B. R.; Holan, G. Int. Pat. Appl. WO 95/34595, Dec 21, 1995.
57. See, for example: (a) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H. B.; Jaworek, W.; Vogue, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Tomalia, D. A.; Durst, H. D. Top. Curr. Chem. 1993, 165, 193. (d) Tomalia, D. A. Adv. Mater. 1994, 6, 529. (e) Issberner, J.; Moors, R.; Vogtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (f) Newlome, G. R.; Moorefield, C. N.; Baker, G. R. Aldrichimica Acta 1992, 25, 31. (g) Service, R. F. Science 1995, 267, 458. (h) Matthews, B. R.; Holan, G. Int. Pat. Appl. WO 95/34595, Dec 21, 1995.
58. See, for example: (a) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H. B.; Jaworek, W.; Vogue, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Tomalia, D. A.; Durst, H. D. Top. Curr. Chem. 1993, 165, 193. (d) Tomalia, D. A. Adv. Mater. 1994, 6, 529. (e) Issberner, J.; Moors, R.; Vogtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (f) Newlome, G. R.; Moorefield, C. N.; Baker, G. R. Aldrichimica Acta 1992, 25, 31. (g) Service, R. F. Science 1995, 267, 458. (h) Matthews, B. R.; Holan, G. Int. Pat. Appl. WO 95/34595, Dec 21, 1995.
59. See, for example: (a) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H. B.; Jaworek, W.; Vogue, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Tomalia, D. A.; Durst, H. D. Top. Curr. Chem. 1993, 165, 193. (d) Tomalia, D. A. Adv. Mater. 1994, 6, 529. (e) Issberner, J.; Moors, R.; Vogtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (f) Newlome, G. R.; Moorefield, C. N.; Baker, G. R. Aldrichimica Acta 1992, 25, 31. (g) Service, R. F. Science 1995, 267, 458. (h) Matthews, B. R.; Holan, G. Int. Pat. Appl. WO 95/34595, Dec 21, 1995.
60. 10d XPS Anal. of 2: found (S/C), 1:9.8. calcd (S/C), 1:10. TGA Anal. of 2: weight loss (%) between 180 and 280°C owing to the cleavage of S-O bond, found, 32.3; calcd, 34.6.
61. Dai, L.; White, J. W. Polymer 1997, 38, 775 and references therein.
62. Hopkins, A. R.; Rasmussen, P. G.; Basheer, R. A. Macromolecules 1996, 29, 7838.
63. (a) Kohlman, R. S.; Tanner, D. B.; Ihas, G. G.; Min, Y. G.; MacDiarmid, A. G.; Epstein, A. J. Synth. Met. 1997, 84, 709 and references therein.
64. (b) Holland, E. R.; Pomfret, S. J.; Adams, P. N.; Abell, L.; Monkman, A. P. Synth. Met. 1997, 84, 777.
65. See, for example: (a) Imahori, H.; Sakata, Y. Adv. Mater. 1997, 9, 537. (b) Schlebusch, C.; Kessler, B.; Cramm, S.; Eberhardt, W. Synth. Met. 1996, 77, 151. (c) Lee, S. B.; Zakhidov, A. A.; Khairullin, I. I.; Sokolov, V. Y.; Khabibullaev, P. K.; Tada, K.; Yoshimoto, K.; Yoshino, K. Synth. Met. 1996, 77, 155. (d) Dai, L. J. Phys. Chem. 1992, 96, 6469. (e) Sariciftci, N. S. Prog. Quantum Electron. 1995, 79, 131 and references therein.
66. See, for example: (a) Imahori, H.; Sakata, Y. Adv. Mater. 1997, 9, 537. (b) Schlebusch, C.; Kessler, B.; Cramm, S.; Eberhardt, W. Synth. Met. 1996, 77, 151. (c) Lee, S. B.; Zakhidov, A. A.; Khairullin, I. I.; Sokolov, V. Y.; Khabibullaev, P. K.; Tada, K.; Yoshimoto, K.; Yoshino, K. Synth. Met. 1996, 77, 155. (d) Dai, L. J. Phys. Chem. 1992, 96, 6469. (e) Sariciftci, N. S. Prog. Quantum Electron. 1995, 79, 131 and references therein.
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