New synthetic routes to alkyl-substituted and functionalized perylenes

Liebigs Annales

Volumn , Issue 2, 1997, Pages 395-407

  Schlichting, Peter ^a   Rohr, Ulrike ^a   Müllen, Klaus ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

Arenes; Dyes; Fluorescent dyes; Palladium catalyzed coupling; Perylenes

Indexed keywords

EID: 0344397678     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970218     Document Type: Article

References (67)

1. H. Zollinger, Color Chemistry, VCH Verlagsgesellschaft, Weinheim, 1987.
2. [2a] Y. Nagao, T. Misono, Bull. Chem. Soc. Jpn. 1979, 52, 1723-1726.
3. [2b] Y. Nagao, T. Misono, Bull. Chem. Soc. Jpn. 1981, 54, 1575-1576.
4. [2c] H. Langhals, Chimia 1994, 48, 503-505.
5. C. I. Solvent Green 5, Colour Index Nr. CI59075, 1972, Colour Index 5, 3632.
6. [4a] Y. Nagao, T. Misono, Dyes Pigm. 1984, 5, 171-188.
7. [4b] A. Rademacher, S. Märkle, H. Langhals, Chem. Ber. 1982, 115, 2927-2934.
8. [5a] H. E. Zieger, J. E. Rosenkranz, J. Org. Chem. 1964, 29, 2469-2471.
9. [5b] H. E. Zieger, J. Org. Chem. 1966, 31, 2977-2981.
10. [6a] M. Lamotte, J. Pereyre, Joussout-Dubien, R. Lapouyade, J. Photochem. 1986, 38, 177-180.
11. [6b] D. A. Peake, A. R. Oyler, K. E. Heikkila, R. J. Liukkonen, E. C. Engraft, R. M. Carlson, Synth. Commun. 1983, 13, 21-26.
12. [6c] H. E. Zieger, E. M. Laski, Tetrahedron Lett. 1966, 32, 3801-3804.
13. U. Anton, C. Göltner, K. Müllen, Chem. Ber. 1992, 125, 2325-2330.
14. [8a] L. B. Johannson, J. G. Molotkovsky, L. D. Bergelson, J. Am. Chem. Soc. 1987, 109, 7374-7381.
15. [8b] A. Minsky, A. Y. Meyer, M. Rabinowitz, J. Am. Chem. Soc. 1982, 104, 2475-2482.
16. [8c] K.-H. Koch, K. Müllen, Chem. Ber. 1991, 124, 2091-2100.
17. W. Jaworek, F. Vögtle, Chem. Ber. 1991, 124, 347-352.
18. [10a] C. Göltner, Ph. D. Thesis, University of Mainz, 1994.
19. [10b] C. Göltner, D. Pressner, K. Müllen, H.-W. Spieß, Angew. Chem. 1993, 105, 1722-1724.
20. [10c] D. Pressner, C. Göltner, H. W. Spieß, K. Müllen, Ber. Bunsenges. Phys. Chem. 1993, 97, 1362-1365.
21. [11a] U. Anton, K. Müllen, Makromol. Chem. Rapid Commun. 1993, 14 (4), 223-229.
22. [11b] U. Anton, K. Müllen, Macromolecules 1993, 26, 1248-1253.
23. H. Kamowaga, J. Polym. Sci., Part A-1 1972, 10, 1345-1351.
24. B. Loer, H. Kerrmann, German Patent 1973, 2137288.
25. Y. Shirota, I.-R. Jeon, N. Noma, Synth. Met. 1993, 55-57, 803-808.
26. Y. Shirota, N. Noma, Y. Shimizu, H. Kaneca, I.-R. Jeon, K. Numa, T. Kakuta, H. Yasui, K. Namba, Synth. Met. 1991, 41-43, 3031-3036.
27. I.-R. Jeon, N. Noma, Y. Shirota, Bull. Chem. Soc. Jpn. 1992, 65, 1062-1066.
28. I.-R. Jeon, N. Noma, Y. Shirota, Mol. Cryst. Liq. Cryst. 1990, 190, 1-7.
29. H. Langhals, Chem. Phys. Lett. 1988, 150, 321-324.
30. I.-R. Jeon, N. Noma, R. F. C. Claridge, Y. Shirota, Polymer J. 1992, 24, 273-279.
31. A. Zinke, H. Unterkreuter, Monatsh. Chem. 1919, 40, 405-410.
32. A. Pongartz, Monatsh. Chem. 1927, 48, 585-591.
33. M. J. S. Dewar, T. Mole, J. Am. Chem. Soc. 1956, 1441-1443.
34. L. Eberson, F. Radner, Acta Chem. Scand., Ser. B 1985, 39, 357-374.
35. A. Nordbotten, L. K. Sydnes, T. Greibokk, Acta. Chem. Scand., Ser. B 1948, 38, 701-706.
36. C. Marschalk, Bull. Soc. Chim. Fr. 1927, 41, 74-81.
37. D. R. P. 408513, 1922.
38. R. Iden, G. Seybold, A. Stange, H. Eilingsfeld, Forschungsbericht-BMFT 84 1984.
39. J. L. Looker, J. Org. Chem. 1972, 37, 3379-3381.
40. H. J. Shine, C. Ristagno, J. Org. Chem. 1972, 37, 3424-3426.
41. M. T. Stephenson, H. J. Shine, J. Org. Chem. 1986, 46, 3139-3141.
42. J. I. G. Cadogan, D. Roy, D. M. Smith, J. Chem. Soc. (C) 1966, 1249-1250.
43. D. A. Buckley, L. A. Teuscher, Br. Polym. J. 1980, 55-56.
44. A. Zinke, T. Linner, O. Wolfbauer, Ber. Dtsch. Chem. Ges. 1925, 58, 323-329.
45. A. Zinke, K. Funke, N. Lorber, Ber. Dtsch. Chem. Ges. 1927, 60, 577-581.
46. R. H. Mitchell, Y.-H. Lai, R. V. Williams, J. Org. Chem. 1979, 44, 4733-4735.
47. Although 3,9 and 3,10 isomers are present, only the 3,9 isomer is shown in the scheme for the sake of simplicity. This refers to all formula schemes in this paper.
48. K. Sonogashira, Y. Tohda; N. Haeihara, Tetrahedron Lett. 1975, 50, 4467-4470.
49. L. Cassar, J. Organomet. Chem. 1975, 93, 253-257.
50. H. A. Dieck, F. R. Heck, J. Organomet. Chem. 1975, 93, 259-263.
51. M. Alami, F. Ferri, G. Linstrumelle, Tetrahedron Lett. 1993, 34, 6403-6406.
52. M. Moroni, J. Le Moigne, S. Luzzati, Macromolecules 1994, 27, 562-571.
53. A. Böhm, BASF AG Ludwigshafen, personal communication, 1995; The synthesis is described in the experimental section.
54. A. Böhm, BASF AG Ludwigshafen, unpublished results, 1995.
55. [7].
56. Field desorption is a very soft method of ionization. Due to the low energy excess and short stay of the ions in the ion source no fragmentation or rearrangement takes place and so only the molecular ion peak is detected. The molecular ion peak shows a characteristic distribution of mass peaks due to the presence of different isotopes in the molecules. As one can use directly the reaction mixture for the measurement this method proved to be the easiest and fastest to controll the course of hydrogenation.
57. D. Pressner, C. Göltner, H.-W. Spieß, K. Müllen, Acta Polymer. 1994, 45, 188-195.
58. The results of this work were presented at the 24. Freiburger Arbeitstagung Flüssigkristalle 5.-7. April 1995:
59. P. Schlichting, U. Rücker, H. W. Spiess, K. Müllen, "Molecular Order and Dynamics of Thermotropic Liquid Crystals Based on the Perylene Skeleton".
60. R. Lapuyade, J. Pereyre, P. Garrigues, C. R. Acad. Sci.: Ser. 2 1986, 303, 903-906 (1986).
61. Yu. G. Molotkovskii, L. D. Bergeisen, Bioorganicheskaya Khimiya 1982, 8, 1256-1262
62. (Chem. Abstr. 1983, 98, 53367e).
63. For this purpose, polymerizable building blocks such as acryloyl chloride or methacryloyl chloride (for example), will be treated with the alcohols 37a or 41a or with the amine 44, or p-hydroxystyrene will be coupled with the acids 37b or 41b. The resulting perylene monomers may then be converted into polymers by radical polymerization. Results in this field will be published soon by our group.
64. [51a] Y. Tanizaki, T. Yoshinaga, H. Hiratsuka, Spectrochim. Acta. 1978, A34, 205-210.
65. [51b] R. N. Jones, Chem. Rev. 1943, 32, 1-46.
66. [51c] D. Peters, J. Chem. Soc. 1957, 646-651.
67. D. D. Perrin, W. L. F. Armarego, D. R. Perrin, Purification of Laboratory Chemicals, 2nd ed., Pergamon Press, Frankfurt, 1987.