Synthesis of symmetrically and unsymmetrically para-functionalized p-quaterphenylenes

Synthesis

Volumn , Issue 4, 2007, Pages 613-621

  Schiek, Manuela ^a   Al Shamery, Katharina ^a   Lützen, Arne ^b  

^a UNIVERSITY OF OLDENBURG   (Germany)

^b UNIVERSITY OF BONN   (Germany)

Author keywords

Cross coupling reaction; Oligo p phenylenes; Rod like molecules; Suzuki

Indexed keywords

CROSS-COUPLING REACTIONS; OLIGO-P-PHENYLENES; ROD-LIKE MOLECULES; SUZUKI;

AGGLOMERATION; FUNCTIONAL GROUPS; OPTICAL PROPERTIES; SELF ASSEMBLY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

OLEFINS;

1 (2,5 DIMETHYL 1H PYRROLE) 4'' NITRO 4,1':4',1'' TERPHENYLENE; 1 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLYL) 4'' METHOXY 4,1:4',1'' TERPHENYLENE; 1 AMINO 4''' METHOXY 4,1':4',1'':4'',1''' QUATERPHENYLENE; 1 BROMO 4'' METHOXY 4,1':4',1'' TERPHENYLENE; 1 CHLORO 4''' METHOXY 4,1':4',1'':4'',1''' QUATERPHENYLENE; 1 CYANO 4'' BROMO 4',1'' TERPHENYLENE; 1 IODO 4'' NITRO 4,1':4',1'' TERPHENYLENE; 1,4''' DI N.N DIMETHYLAMINO 4,1':4',1'':4'',1''' QUATERPHENYLENE; 1,4''' DIAMINO 4,1':4',1'':4'',1''' QUATERPHENYLENE; 1,4''' DICHLORO 4,1':4'',1''' QUATERPHENYLENE; 1,4''' DICYANO 4,1':4'',1''' QUATERPHENYLENE; 1,4''' DIMETHOXY 4,1':4'',1''' QUATERPHENYLENE; 1,4''' DINITRO 4,1':4',1'':4'',1''' QUATERPHENYLENE; 4 (2,5 DIMETHYL 1H PYRROLE) 4' AITROBIPHENYL; 4 (2,5 DIMETHYL 1H PYRROLE) 4' CHLOROBIPHENYL; 4 (2,5 DIMETHYL 1H PYRROLE) 4' CYANOBIPHENYL; 4 (2,5 DIMETHYL 1H PYRROLE) 4' METHOXYBIPHENYL; 4 (2,5 DIMETHYL 1H PYRROLE) 4' N.,N DIMETHYLAMINOBIPHENYL; 4 (2,5 DIMETHYL 2H PYRROLE) 4' BROMOBIPHENYL; 4 CHLORO 4' IODOBIPHENYL; 4 CYANO 4' IODOBIPHENYL; 4 CYANO 4''' EMTHOXY 1,1':4',1'':4'',1''' QUATERPHENYLENE; 4 IODO 4' METHOXYBIPHENYL; 4 IODO 4' NITROBIPHENYL; 4 N,N DIMETHYLAMINO 4, IODODIPHENYL; BENZENE DERIVATIVE; BIPHENYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; MORPHOLOGY; SUZUKI REACTION; SYNTHESIS; VAPOR;

EID: 33947495777     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-965891     Document Type: Article

References (122)

1. (a) Müllen, K.; Wegner, G. Electronic Materials: The Oligomer Approach; Wiley-VCH: Weinheim, 1998.
2. (b) Fichou, D. Handbook of Oligo- and Polythiophenes; Wiley-VCH: Weinheim, 1999.
3. (c) Nalva, H. S. Handbook of Advanced Electronic and Photonic Materials and Devices; Academic Press: San Diego, 2000.
4. (d) Müllen, K.; Scherf, U. Organic Light Emitting Devices - Synthesis, Properties and Applications; Wiley-VCH: Weinheim, 2006.
5. (e) Klauk, H. Organic Electronics - An Industrial Perspective; Wiley-VCH: Weinheim, 2006.
6. (a) Schwab, P. F. H.; Levin, M. D.; Michl, J. Chem. Rev. 1999, 99, 1863.
7. (b) Schwab, P. F. H.; Smith, J. R.; Michl, J. Chem. Rev. 2005, 105, 1197.
8. Ziegler, G. In Handbook of Organic Conductive Molecules and Polymers, Vol. 3; Nalwa, H. S., Ed.; Wiley: New York, 1997, Chap. 13.
9. (a) Krause, B.; Dürr, A. C.; Ritley, K.; Schreiber, F.; Dosch, H.; Smilgies, D. Phys. Rev. B: Condens. Matter Mater. Phys. 2002, 66, 235404.
10. (b) Würthner, F. Chem. Commun. 2004, 1564.
11. Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891.
12. James, D. K.; Tour, J. M. Top. Curr. Chem. 2005, 257, 33.
13. (a) Resel, R. Thin Solid Films 2003, 433, 1.
14. (b) Balzer, F.; Rubahn, H.-G. Adv. Funct. Mater. 2005, 14, 17.
15. (c) Balzer, F.; Rubahn, H.-G. Phys. Unserer Zeit 2005, 36, 36.
16. (a) Witte, G.; Woell, C. J. Mater. Res. 2004, 19, 1889.
17. (b) Hertel, D.; Müller, C. D.; Meerholz, K. Chem. Unserer Zeit 2005, 39, 336.
18. (a) Balzer, F.; Rubahn, H.-G. Appl. Phys. Lett. 2001, 79, 2860.
19. (b) Balzer, F.; Rubahn, H.-G. Surf. Sci. 2002, 507, 588.
20. Yanagi, H.; Morikawa, T. Appl. Phys. Lett. 1999, 75, 187.
21. (a) Balzer, F.; Bordo, V. G.; Simonsen, A. C.; Rubahn, H.-G. Appl. Phys. Lett. 2003, 82, 10.
22. (b) Balzer, F.; Bordo, V. G.; Simonsen, A. C.; Rubahn, H.-G. Phys. Rev. B: Condens. Matter Mater. Phys. 2003, 67, 115408.
23. (a) Quochi, F.; Cordelia, F.; Orri, R.; Communal, J. E.; Verzeroli, P.; Mura, A.; Bongiovanni, G.; Andreev, A.; Sitter, H.; Sariciftci, N. S. Appl. Phys. Lett. 2004, 84, 4454.
24. (b) Quochi, F.; Cordelia, F.; Mura, A.; Bongiovanni, G.; Balzer, F.; Rubahn, H.-G. J. Phys. Chem. B 2005, 109, 21690.
25. (c) Quochi, F.; Cordella, F.; Mura, A.; Bongiovanni, G.; Balzer, F.; Rubahn, H.-G. Appl. Phys. Lett. 2006, 88, 041106.
26. Kjelstrup-Hansen, J.; Henrichsen, H. H.; Boggild, P.; Rubahn, H.-G. Thin Solid Films 2006, 515, 827.
27. Henrichsen, H. H.; Kjelstrup-Hansen, J.; Engstroem, D.; Clausen, C H.; Bøggild, P.; Rubahn, H.-G. Appl. Phys. A 2006, submitted.
28. Kjelstrup-Hansen, J.; Bøggild, P.; Rubahn, H.-G. J. Phys. C 2006, submitted.
29. (a) Schiek, M.; Lützen, A.; Koch, R.; Al-Shamery, K.; Balzer, F.; Frese, R.; Rubahn, H.-G. Appl. Phys. Lett. 2005, 86, 153107.
30. (b) Schiek, M.; Lützen, A.; Al-Shamery, K.; Balzer, F.; Rubahn, H.-G. Surf. Sci. 2006, 600, 4030.
31. (c) Schiek, M.; Lützen, A.; Al-Shamery, K.; Balzer, F.; Rubahn, H.-G. Cryst. Growth Des. 2006, accepted for publication.
32. Brewer, J.; Schiek, M.; Lützen, A.; Al-Shamery, K.; Rubahn, H.-G. Nano Lett. 2006, 6, 2656.
33. Schmidt, H.; Schultz, G. Justus Liebigs Ann. Chem. 1880, 203, 129.
34. (a) Scheinbaum, M. L. J. Chem. Soc., Chem. Commun. 1969, 1235.
35. (b) Pavlopoulos, T. G.; Hammond, P. R. J. Am. Chem. Soc. 1974, 96, 6568.
36. (a) Keegstra, M. A.; De Feyter, S.; De Schryver, F. C.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 774;
37. Angew. Chem. 1996, 108, 830.
38. (b) Iyer, V. S.; Wehmeier, M.; Brand, J. D.; Keegstra, M. A.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 1604;
39. Angew. Chem. 1997, 109, 1676.
40. (c) Müller, M.; Iyer, V. S.; Kübel, C.; Enkelmann, V.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 1607;
41. Angew. Chem. 1997, 109, 1679.
42. (d) Fechtenkötter, A.; Saalwächter, K.; Harbison, M. A.; Müllen, K.; Spiess, H. W. Angew. Chem. Int. Ed. 1999, 38, 3039;
43. Angew. Chem. 1999, 111, 3224.
44. (e) Ito, S.; Herwig, P. T.; Böhme, T.; Rabe, J. P.; Rettig, W.; Müllen, K. J. Am. Chem. Soc. 2000, 122, 7698.
45. (a) Stille, J. K.; Rakutis, R. O.; Mukamal, H.; Harris, F. W. Macromolecules 1968, 1, 431.
46. (b) Morgenroth, F.; Reuther, E.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 631;
47. Angew. Chem. 1997, 109, 647.
48. (c) Wiesler, U.-M.; Müllen, K. Chem. Commun. 1999, 2293.
49. (d) Dötz, F.; Brand, J. D.; Ito, S.; Gherghel, L.; Müllen, K. J. Am. Chem. Soc. 2000, 122, 7707.
50. (e) Wiesler, U.-M.; Berresheim, A. J.; Morgenroth, F.; Lieser, G.; Müllen, K. Macromolecules 2001, 34, 187.
51. (f) Weil, T.; Wiesler, U.-M.; Herrmann, A.; Bauer, R.; Hofkens, J.; De Schryver, F. C.; Müllen, K. J. Am. Chem. Soc. 2001, 123, 8101.
52. (g) Simpson, C. D.; Brand, J. D.; Berresheim, A. J.; Przybilla, L.; Rader, H. J.; Müllen, K. Chem. Eur. J. 2002, 8, 1424.
53. Subramaniam, G.; Gilpin, R. K. Synthesis 1992, 1232.
54. (a) Hart, H.; Harada, K. Tetrahedron Lett. 1985, 26, 29.
55. (b) Hart, H.; Harada, K.; Frank Du, C.-J. J. Org. Chem. 1985, 50, 3104.
56. (c) Harada, K.; Hart, H.; Frank Du, C.-J. J. Org. Chem. 1985, 50, 5524.
57. (d) Frank Du, C.-J.; Hart, H.; Ng, K.-K. D. J. Org. Chem. 1986, 51, 3162.
58. (a) Rebmann, A.; Zhou, J.; Schuler, P.; Stegmann, H. B.; Rieker, A. J. Chem. Res., Synop. 1996, 318.
59. (b) Rebmann, A.; Zhou, J.; Schuler, P.; Rieker, A.; Stegmann, H. B. J. Chem. Soc., Perkin Trans. 2 1997, 1615.
60. Harley-Mason, J.; Mann, F. G. J. Chem. Soc. 1940, 1379.
61. (a) Metal-catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
62. (b) Lie, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon Press, Elsevier: Amsterdam, 2000.
63. (c) Cross-Coupling Reactions; Miyaura, N., Ed.; Springer: Berlin, 2002.
64. (d) For a special issue on cross-coupling reactions, see: Tamao, K.; Hiyama, T.; Negishi, E. J. Organomet. Chem. 2002, 653, 1.
65. For examples of the application of nickel-catalyzed Kharash couplings for the synthesis of oligo-p-phenylenes, see: (a) Saitoh, H.; Saito, K.; Yamamura, Y.; Matsuyama, H.; Kikuchi, K.; Iyoda, M.; Ikemoto, I. Bull. Chem. Soc. Jpn. 1993, 66, 2847.
66. (b) Ung, V. A.; Bardwell, D. A.; Jeffery, J. C.; Maher, J. P.; McCleverty, J. A.; Ward, M. D.; Williamson, A. Inorg. Chem. 1996, 35, 5290.
67. (c) Abdul-Rahman, A.; Amoroso, A. A.; Branston, T. N.; Das, A.; Maher, J. P.; McCleverty, J. A.; Ward, M. D.; Wlodarczyk, A. Polyhedron 1997, 16, 4353.
68. For examples of the application of palladium-catalyzed Kharash couplings for the synthesis of oligo-p-phenylenes, see: (a) Kallitsis, J. K.; Kakali, F.; Gravalos, K. G. Macromolecules 1994, 27, 4509.
69. (b) Kallitsis, J. K.; Gravalos, K. G.; Hilberer, A.; Hadziioannou, G. Macromolecules 1997, 30, 2989.
70. (c) Kauffmann, J. M. Synthesis 1999, 918.
71. (d) Rathore, R.; Burns, C. L.; Deselnicu, M. I. Org. Lett. 2001, 3, 2887.
72. For examples of the application of palladium-catalyzed Suzuki couplings for the synthesis of oligo-p-phenylenes, see: (a) Liess, P.; Hensel, V.; Schlüter, A.-D. Liebigs Ann. 1996, 1037.
73. (b) Fran, J.; Karakaya, B.; Schäfer, A.; Schlüter, A. D. Tetrahedron 1997, 53, 15459.
74. (c) Hensel, V.; Schlüter, A.-D. Chem. Eur. J. 1999, 5, 421.
75. (d) Sakai, N.; Brennan, K. C.; Weiss, L. A.; Matile, S. J. Am. Chem. Soc. 1997, 119, 8726.
76. (e) Ghebremariam, B.; Matile, S. Tetrahedron Lett. 1998, 39, 5335.
77. (f) Ghebremariam, B.; Sidorov, V.; Matile, S. Tetrahedron Lett. 1999, 40, 1445.
78. (g) Winum, J.-Y.; Matile, S. J. Am. Chem. Soc 1999, 121, 7961.
79. (h) Robert, F.; Winum, J.-Y.; Sakai, N.; Gerard, D.; Matile, S. Org. Lett. 2000, 2, 37.
80. (i) Sakai, N.; Gerard, D.; Matile, S. J. Am. Chem. Soc. 2001, 123, 2517.
81. (j) Sakai, N.; Matile, S. J. Am. Chem. Soc. 2002, 124, 1184.
82. (k) Galda, P.; Rehahn, M. Synthesis 1996, 614.
83. (l) Kim, S.; Jackiw, J.; Robinson, E.; Schanze, K. S.; Reynolds, J. R. Macromolecules 1998, 31, 964.
84. (m) Goldfinger, M. B.; Crawford, K. B.; Swager, T. M. J. Org. Chem. 1998, 63, 1676.
85. (n) Konstandakopoulou, F. D.; Gravalos, K. G.; Kallitsis, J. K. Macromolecules 1998, 31, 5264.
86. (o) Morikawa, A. Macromolecules 1998, 31, 5999.
87. (p) Schlicke, B.; Belser, P.; De Cola, L.; Sabbioni, E.; Balzani, V. J. Am. Chem. Soc. 1999, 121, 4207.
88. (q) Taylor, P. N.; O'Connell, M. J.; McNeill, L. A.; Hall, M. J.; Alpin, R. T.; Anderson, H. L. Angew. Chem. Int. Ed. 2000, 39, 3456;
89. Angew. Chem. 2000, 112, 3598.
90. (r) Read, M. W.; Escobedo, J. O.; Willis, D. M.; Beck, P. A.; Strongin, R. M. Org. Lett. 2000, 2, 3201.
91. (s) Hwang, S.-W.; Chen, Y. Macromolecules 2001, 34, 2981.
92. (t) Park, J.-W.; Ediger, M. D.; Green, M. M. J. Am. Chem. Soc. 2001, 123, 49.
93. (u) Deng, X.; Mayeux, A.; Cai, C. J. Org. Chem. 2002, 67, 5279.
94. (v) Lightowler, S.; Hird, M. Chem. Mater. 2004, 16, 3963.
95. (w) Lightowler, S.; Hird, M. Chem. Mater. 2005, 27, 5538.
96. (a) Percec, V.; Okita, S. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 877.
97. (b) Morikawa, A. Macromolecules 1998, 31, 5999.
98. (c) Li, Z. H.; Wong, M. S.; Tao, Y.; D'Iorio, M. J. Org. Chem. 2004, 69, 921.
99. (d) Lee, M.; Jang, C.-J.; Ryu, J.-H. J. Am. Chem. Soc. 2004, 126, 8082.
100. (e) Ryu, J.-H.; Jang, C.-J.; Yoo, Y.-S.; Lim, S.-G.; Lee, M. J. Org. Chem. 2005, 70, 8956.
101. (f) Welter, S.; Salluce, N.; Benetti, A.; Rot, N.; Belser, P.; Sonar, P.; Grimsdale, A. C.; Müllen, K.; Lutz, M.; Spek, A. L.; de Cola, L. Inorg. Chem. 2005, 44, 4706.
102. Broutin, P. E.; Cerna, I.; Campaniello, M.; Leroux, F.; Colobert, F. Org. Lett. 2004, 6, 4419.
103. (a) Thiemann, F.; Piehler, T.; Haase, D.; Saak, W.; Lützen, A. Eur. J. Org. Chem. 2005, 1991.
104. (b) Pushechnikov, O.; Ivonin, S. P.; Chaikovskaya, A. A.; Kudrya, T. N.; Pirozhenko, V. V.; Tolmachev, A. A. Chem. Heterocycl. Compd. 1999, 35, 1313; without synthetic details or characterization.
105. In fact this compound is commercially available and its synthesis has been previously described using different approaches, see: (a) Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 37, 2703.
106. (b) Spivey, A. C.; Diaper, C. M.; Rudge, A. J. Chem. Commun. 1999, 835.
107. (c) Spivey, A. C.; Diaper, C. M.; Adams, H.; Rudge, A. J. J. Org. Chem. 2000, 65, 5253.
108. (d) Sinclair, D. J.; Sherburn, M. S. J. Org. Chem. 2005, 70, 3730. However, no NMR or MS data were provided.
109. In fact this compound is commercially available and its synthesis has been previously described using a different approach, see ref. 33a. However, no NMR or MS data were provided.
110. This compound has been previously synthesized using a different approach, see: (a) Pummerer, R.; Sellsberger, L. Ber. Dtsch. Chem. Ges. B. 1931, 64, 2477.
111. (b) McNamara, J. M.; Gleason, W. B. J. Org. Chem. 1976, 41, 1071. However, no NMR or MS data were provided.
112. This compound is commercially available and its synthesis has been previously described using different approaches, see: (a) Sedov, A. M.; Sergeeva, A. A.; Novikov, A. N. Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 1970, 13, 591; Chem. Abstr. 1970, 73, 87559.
113. (b) Rottaelander, M.; Palmer, N.; Knochel, P. Synlett 1996, 573.
114. (c) Sinclair, D. J.; Sherburn, M. S. J. Org. Chem. 2005, 70, 3730. However, no NMR or MS data were provided.
115. This compound has been previously synthesized using a different approach, see: (a) Theilacker, W.; Schmid, W. Chem. Ber. 1951, 84, 204.
116. (b) Theilacker, W.; Berger, W.; Popper, P. Chem. Ber. 1956, 89, 970. However, no NMR or MS data were provided.
117. This compound has been previously synthesized using a different approach, see: Amatore, C.; Jutand, A.; Negre, S.; Fauvarque, J. F. J. Organomet. Chem. 1990, 390, 389.
118. This compound has been previously synthesized using a different approach, see: Novikov, A. N.; Khalimova, T. A. Zh. Vses. Khim. O-va. im. D. I. Mendeleeva 1962, 7, 698; Chem. Abstr. 1962, 58, 66196. However, no NMR or MS data were provided.
119. This compound has been previously synthesized using a different approach, see ref. 25, 27b and 27c. See also: Ronlan, A.; Coleman, J.; Hammerich, O.; Parker, V. D. J. Am. Chem. Soc. 1974, 96, 845.
120. This compound has been previously synthesized using a different approach though no spectroscopical data were given, see ref. 30a and: (a) Jutand, A.; Mosleh, A. Synlett 1993, 568.
121. (b) Jutand, A.; Mosleh, A. J. Org. Chem. 1997, 62, 261.
122. The formation of this compound has been postulated as an undesired by-product in the synthesis of triarylmethane dyes; however, no analytical or structural data was given, see: Theilacker, W.; Berger, W.; Popper, P. Chem. Ber. 1956, 89, 970.