Synthesis and characterization of a new conjugated aromatic poly(azomethine) derivative based on the 3′,4′-dibutyl-α-terthiophene building block

Macromolecules

Volumn 29, Issue 9, 1996, Pages 3147-3156

  Wang, Chenggang ^a   Shieh, Seaver ^a   LeGoff, Eugene ^a   Kanatzidis, Mercouri G ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARACTERIZATION; DERIVATIVES; ELECTRON SPIN RESONANCE SPECTROSCOPY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOLUMINESCENCE; POLYCONDENSATION; POLYCRYSTALLINE MATERIALS; SULFURIC ACID; SYNTHESIS (CHEMICAL); ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

CONCENTRATED SULFURIC ACID; LEWIS ACIDS; OPTICAL BAND GAP; POLYAZOMETHINE; PROTONATION;

AROMATIC POLYMERS;

EID: 0030126144     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma9514131     Document Type: Article

References (62)

1. (a) Bredas, J. L., Chance, R. R., Eds. Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics, and Molecular Electronics; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1990.
2. (b) Skotheim, T. A., Ed. Handbook of Conducting Polymers; Marcel Dekker. New York, 1986.
3. (c) Kanatzidis, M. G. Chem., Eng. News 1990, 68, (Dec 3), 36-54.
4. (d) Roncali, J. Chem. Rev. 1992, 92, 711
5. Prasad, P. N.; Williams, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; Wiley: New York, 1991.
6. (a) Su W. P.; Schrieffer, J. R.; Heeger, A. J. Phys. Rev. Lett. 1979, 42, 1698-1701.
7. (b) Park, Y. W.; Heeger, A. J.; Druy, M. A.; MacDiarmid, A. G. J. Chem. Phys. 1980, 73, 946-957.
8. Frommer, J. E.; Chance, R. R. Encyl. Polym. Sci. Eng. 1985, 5, 462-507.
9. (a) Antoun, S.; Karasz, F. E.; Lenz, R. W. J. Polym. Sci., Part A: Polym. Chem. 1988, 26, 1800-1817.
10. (b) Eckhardht, H.; Shacklette, L. W.; Jen, K. Y.; Elsenbaumer, R. L. J. Chem. Phys. 1989, 91, 1301-1315.
11. (a) Chiang, J. C.; MacDiarmid, A. G. Synth. Met. 1986, 13, 193.
12. (b) Epstein, A. J.; Ginder, J. M.; Zuo, F.; Bigelow, R. W.; Woo, H.-S.; Tanner, D. B.; Richter, A. F.; Huang, W. S.; MacDiarmid, A. G. Synth. Met. 1987, 18, 303-309.
13. (a) Astruias, G. E.; MacDiarmid, A. G.; McCall, R. P.; Epstein, A. J. Synth. Met. 1989, 29, E157-E163.
14. (b) Sun, Y., MacDiarmid, A. G.; Epstein, A. J. J. Chem. Soc., Chem. Commun. 1990, 529-531.
15. (c) Huang, W. S.; MacDiarmid, A. G.; Epstein, A. J. J. Chem. Soc., Chem. Commun. 1987, 1784-1785.
16. Hauer, C. R.; King, G. S.; McCool, E. L.; Euler, W. B.; Ferrara, J. D.; Youngs, W. J. J. Am. Chem. Soc. 1987, 109, 5760-5765.
17. Cao, Y.; Li, S. J. Chem. Soc., Chem. Commun. 1988, 937.
18. (a) Euler, W. B.; Roberts, J. E. Synth. Met. 1989, 29, E546.
19. (b) Chaloner-Gill, B.; Cheer, C. J.; Roberts, J. E.; Euler, W. B. Macromolecules 1990, 23, 4597.
20. (c) Chaloner-Gill, B.; Euler, W. B.; Roberts, J. E. Macromolecules 1991, 24, 3074-3080.
21. Adams, R.; Bullock, J. E.; Wilson, W. C. J. Am. Chem. Soc. 1923, 45, 521.
22. D'Alelio, G. F.; Schoenig, R. K.; J. Macromol. Sci. Rev.: Macromool. Chem. 1969, C3, 105-234.
23. Morgan, P. W.; Kwolek, S. L.; Pletcher, T. C. Macromolecules 1987, 20, 729-739.
24. (a) Millaud, B.; Thierry, A.; Skoulios, A. Mol. Cryst. Liq. Cryst. Lett. 1978, 41, 263.
25. (b) Noel, C.; Billard, J. Mol. Cryst. Liq. Cryst. Lett. 1978, 41, 260-262.
26. (a) Yang, C.J.; Jenekhe, S. A. Macromolecules 1995, 28, 1180-1196.
27. (b) Jenekhe, S. A.; Yang, C.-J.; Vanherzeele, H.; Meth, J. S. Chem. Mater. 1991, 3, 987-989.
28. (a) Barbarin, F.; Blance, J. P.; Dugay, M.; Fabre, C.; Maleysson, C. Synth. Met. 1984/85, 10, 71-78.
29. (b) Li, X.; Li, C.; Li, S. Synth. Met. 1993, 60, 285-288.
30. Lee, K. S.; Won, J. C.; Jung, J. C. Makromol. Chem. 1989, 190, 1547-1552.
31. Park, S.-B., Kim, H.; Zin, W.-C.; Jung, J. C. Macromolecules 1993, 26, 1627-1632.
32. (a) Jenekhe, S. A.; Yang, C.-J. Chem. Mater. 1991, 3, 878-887.
33. (b) Yang, C.-J.; Jenekhe, S. A. Chem. Mater. 1994, 6, 196-203.
34. (a) Wang, C.; Xie, X.; LeGoff, E.; Albritton-Thomas, J.; Kannewurf, C. R.; Kanatzidis, M. G. Synth. Met. 1995, 74, 71-74.
35. (b) Wang, C.; Shieh, S.; LeGoff, E.; Kanatzidis, M. G., manuscript in preparation.
36. Ethanothermal conditions, i.e., ethanol medium over 120 °C and autogenous pressure.
37. During preparation of this paper, a poly(azomethine) constituted of six thienylene and two phenylene segments linked together with azomethines moieties was briefly described in the literature: Destri, S; Masecherpa, M.; Porzio, W. Synth. Met. 1995, 69, 287-288.
38. Agrawal, A. K.; Jenekhe, S. A. Macromolecules 1993, 26, 895-905.
39. (a) Wang, C.; Benz, M. E.; LeGoff, E.; Schindler, J. L.; Kannewurf, C. R.; Kanatzidis, M. G. Polym. Prepr. 1993, 34 (2), 422-423.
40. (b) Wang, C.; Benz, M. E.; LeGoff, E.; Schindler, J. L.; Albritton-Thomas, J.; Kannewurf, C. R.; Kanatzidis, M. G. Chem. Mater. 1994, 6, 401-411.
41. Hydrothermal conditions, i.e., aqueous medium over 100 °C and autogenous pressure. (a) Rabenau, A. Angew. Chem., Int. Ed. Engl. 1985, 24, 1026-1040. (b) Haushalter, R. C.; Mundi, L. A. Chem. Mater. 1992, 4, 31-48. (c) Liao, J.-H.; Kanatzidis, M. G. J. Am. Chem. Soc. 1990, 112, 7400-7402. (d) Liao, J.-H.; Kanatzidis, M. G. Inorg. Chem. 1992, 31, 431-439.
42. Hydrothermal conditions, i.e., aqueous medium over 100 °C and autogenous pressure. (a) Rabenau, A. Angew. Chem., Int. Ed. Engl. 1985, 24, 1026-1040. (b) Haushalter, R. C.; Mundi, L. A. Chem. Mater. 1992, 4, 31-48. (c) Liao, J.-H.; Kanatzidis, M. G. J. Am. Chem. Soc. 1990, 112, 7400-7402. (d) Liao, J.-H.; Kanatzidis, M. G. Inorg. Chem. 1992, 31, 431-439.
43. Hydrothermal conditions, i.e., aqueous medium over 100 °C and autogenous pressure. (a) Rabenau, A. Angew. Chem., Int. Ed. Engl. 1985, 24, 1026-1040. (b) Haushalter, R. C.; Mundi, L. A. Chem. Mater. 1992, 4, 31-48. (c) Liao, J.-H.; Kanatzidis, M. G. J. Am. Chem. Soc. 1990, 112, 7400-7402. (d) Liao, J.-H.; Kanatzidis, M. G. Inorg. Chem. 1992, 31, 431-439.
44. Hydrothermal conditions, i.e., aqueous medium over 100 °C and autogenous pressure. (a) Rabenau, A. Angew. Chem., Int. Ed. Engl. 1985, 24, 1026-1040. (b) Haushalter, R. C.; Mundi, L. A. Chem. Mater. 1992, 4, 31-48. (c) Liao, J.-H.; Kanatzidis, M. G. J. Am. Chem. Soc. 1990, 112, 7400-7402. (d) Liao, J.-H.; Kanatzidis, M. G. Inorg. Chem. 1992, 31, 431-439.
45. 2 1.6 software package by Molecular Simulations Inc., San Diego, CA.
46. Liao, J.-H.; Benz, M.; LeGoff, E.; Kanatzidis, M. G. Adv. Mater. 1994, 6, 135-138.
47. It is known that a partially amorphous material usually has lower density than the fully crystalline version of the material: Mo, Z.; Lee, K.-B.; Moon, Y. B.; Kobayashi, M.; Heeger, A. J.; Wudl, F. Macromolecules 1985, 18, 1972-1977.
48. (a) Jenekhe, S. A.; Johnson, P. O.; Agrawal, A. K. Macromolecules 1989, 22, 3216-3222.
49. (b) Jenekhe, S. A.; Johnson, P. O. Macromolecules, 1990, 23, 4419-4429.
50. (c) Roberts, M. F.; Jenekhe, S. A. Polym. Commun. 1990, 31, 215-217.
51. (d) Osaheni, J. A.; Jenekhe, S. A. Chem. Mater. 1992, 4, 1282-1290.
52. Socrates, G. Infrared Characteristic Group Frequencies; John Wiley & Sons: New York, 1994.
53. Maior, R. M.; Hinkelmann, K.; Eckert, H.; Wudl. F. Macromolecules 1990, 23, 1268-1279.
54. (a) Ward, B.; Chang, C. K.; Young, R. J. Am. Chem. Soc. 1984, 106, 3943-3950.
55. (b) Hanson, L. K.; Chang, C. K.; Ward, B.; Callahan, P. M.; Babcock, G. T.; Head, J. J. Am. Chem. Soc. 1984, 106, 3950-3958.
56. Bakhshi, A. K.; Liegener, C.-M.; Ladik, J. Synth. Met. 1989, 30, 79-85.
57. (a) Wendlandt, W. W.; Hecht, H. G. Reflectance Spectroscopy; Interscience Publishers: New York, 1966.
58. (b) Kotum, G. R. Reflectance Spectroscopv; Springer Verlag: New York, 1969.
59. (c) Tandon, S. P.; Gupta, J. P. Phys. Status Solid 1970, 38, 363-367.
60. 2 → 0.
61. (a) Hay, M. F.; Yang, Y.; Klavetter, F. L. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1994, 35 (1), 293-294.
62. (b) Yang, Z., Sokolik, I.; Karasz, F. E. Macromolecules 1993, 26, 1188-1190.