Novel polyaromatic quinone imines. 2. Synthesis of model compounds and stereoregular poly(quinone imines) from disubstituted anthraquinones

Macromolecules

Volumn 29, Issue 18, 1996, Pages 5835-5842

  Boone, Harold W ^a   Hall Jr , H K ^a  

^a University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARACTERIZATION; MODELS; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYCONDENSATION; POLYMERIZATION; SOLUBILITY; SYNTHESIS (CHEMICAL);

DISUBSTITUTED ANTHRAQUINONES; POLYAROMATIC QUINONE IMINES; POLYQUINONE IMINES; STEREOCHEMISTRY; STERIC INTERACTIONS;

ORGANIC POLYMERS;

EID: 0030213801     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma9602435     Document Type: Article

References (27)

1. (a) Prasad, P. N., Nigam, J. K., Eds. Frontiers of Polymer Research; Plenum: New York, 1991.
2. (b) Epstein, A. J. In Conjugated Polymers; Brédas, J. L., Silbey, R., Eds.; Kluwer Academic Press: Dordrecht, The Netherlands, 1991 p 211.
3. (c) MacDiarmid, A. G.; Epstein, A. J. In Conjugated Polymeric Materials; Brédas, J. L., Chance, R. R., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1990; p 53.
4. Skotheim, T. A., Ed. Handbook of Conductive Polymers; Marcel Dekker: New York, 1986; Vols. I and II.
5. (a) MacDiarmid, A. G.; Mu, S. L.; Somasiri, M. L. D.; Wu, W. Mol. Cryst. Liq. Cryst. 1985, 121, 187.
6. (b) Huang, W. S.; Humphrey, B. D.; MacDiarmid, A. G. J. Chem. Soc., Faraday Trans. 1 1986, 82, 2385.
7. Vachon, D.; Angus, R. O., Jr.; Lu, F. L.; Nowak, M.; Liu, Z. X.; Schaffer, H.; Wudl, F.; Heeger, A. J. Synth. Met. 1987, 18, 297.
8. Wudl, F.; Angus, R. O., Jr.; Lu, F. L.; Allemand, P. M.; Vachon, D. J.; Nowak, M.; Liu, Z. X.; Heeger, A. J. J. Am. Chem. Soc. 1987, 109, 3677.
9. Williams, P. A.; Ellzey, K. A.; Padias, A. B.; Hall, H. K., Jr. Macromolecules 1993, 26, 5820.
10. Hall, H. K., Jr.; Padias, A. B.; Williams, P. A.; Gosau, J.; Boone, H. W.; Park, D. K. Macromolecules 1995, 28, 1.
11. Everaerts, A.; Roberts, S.; Hall, H. K., Jr. J. Polym. Sci., Polym. Chem. 1986, 24, 1703.
12. Hall, H. K., Jr.; Padias, A. B.; Yahagi, I.; Williams, P. A.; Bruck, M. A.; Drujon, X. Macromolecules 1995, 28, 9.
13. Boone, H. W.; Bates, R. B.; Padias, A. B.; Hall, H. K., Jr. J. Org. Chem. 1995, 60. 5279.
14. Boone, H. W.; Hall, H. K., Jr. Unpublished results.
15. (a) Stern, R.; Ballauff, M.; Lieser, G.; Wegner, G. Polymer 1991, 32 (11), 2096.
16. (b) Ballauf, M. Angew. Chem., Int. Ed Engl. 1989, 28, 253.
17. Lu, T.; Hyunsook, K. Y.; Zhang, H.; Bott, S.; Hyunsook, K. Y.; Echegoyen, L.; Gokel, G. W. J. Org. Chem. 1990, 55, 2269.
18. Fang, J.; Tianbao, L.; Hyunsook, K. Y.; Delgado, I.; Geoffry, P.; Hyunsook, K. Y.; Gokel, G. W. J. Org. Chem. 1991, 56, 7059.
19. Echegoyen, L.; Lawson, R. C.; Lopez, C.; de Mendoza, J.; Hafez, Y.; Torres, T. J. Org. Chem. 1994, 59, 3814.
20. Preston, P. N.; Winwick, T. J. Chem. Soc., Perkin Trans. 1 1983, 1439.
21. (a) Stoddart, J. F. Chem. Soc. Rev. 1979, 8, 85.
22. (b) Mark, J. E.; Flory, P. J. J. Am. Chem. Soc. 1965, 87, 1415.
23. The degree of buckling of 15DMAQ is 34° compared to a 26° buckling of DAQ as determined by X-ray crystallographic analysis.
24. Boone, H. W.; Padias, A. B.; Hall, H. K., Jr. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1996, 37 (1), 676.
25. Cameron, D. W.; Feutrill, G. E.; McKay, P. G. Tetrahedron Lett. 1981, 701.
26. Dictionary of Organic Compounds; Eyre and Spottiswoode: London, 1965; Vol. 2, p 1049.
27. Ando, T.; Yamawaki, J.; Kawate, T.; Shinjiro, S.; Hanafusa, T. Bull. Chem. Soc. Jpn. 1982, 55, 2504.