Assembly of π conjugated phosphole azahelicene derivatives into chiral coordination complexes: An experimental and theoretical study

Chemistry - A European Journal

Volumn 16, Issue 20, 2010, Pages 5976-6005

  Graule, Sebastien ^a   Rudolph, Mark ^b   Shen, Wenting ^a   Gareth Williams, J A ^c   Lescop, Christophe ^a   Autschbach, Jochen ^b   Crassous, Jeanne ^a   Réau, Régis ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

^b UNIVERSITY AT BUFFALO   (United States)

^c DURHAM UNIVERSITY   (United Kingdom)

Author keywords

Chiroptical properties; Density functional calculations; Helical structures; P N ligands; Palladium

Indexed keywords

COORDINATION REACTIONS; COPPER COMPOUNDS; DENSITY FUNCTIONAL THEORY; DICHROISM; ORGANIC POLYMERS; PALLADIUM; SELF ASSEMBLY; STEREOCHEMISTRY;

CHIROPTICAL PROPERTIES; COORDINATION GEOMETRY; COORDINATION PROCESS; ELECTRONIC INTERACTIONS; HELICAL STRUCTURES; P-N LIGANDS; PHOTOPHYSICAL PROPERTIES; STRUCTURE PROPERTY RELATIONSHIPS;

X RAY CRYSTALLOGRAPHY;

EID: 77952394738     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903234     Document Type: Article

References (147)

1. a) T. J. Katz, Angew. Chem. 2000, 112, 1997-1999;
2. Angew. Chem. Int. Ed. 2000, 39, 1921-1923;
3. b) A. Urbano, Angew. Chem. 2003, 115, 4116-4119;
4. Angew. Chem. Int. Ed. 2003, 42, 3986-3989;
5. c) R. H. Martin, Angew. Chem. 1974, 86, 727-738;
6. Angew. Chem. Int. Ed. Engl. 1974, 13, 649-660;
7. d) A. Rajca, M. Miyasaka in Functional Organic Materials (Eds.: T. J. J. Müller, U. H. F. Bunz), Wiley- VCH, Weinheim, 2007, pp. 543-577.
8. a) F. Furche, R. Ahlrichs, C. Wachsmann, E. Weber, A. Sobanski, F. Vogtle, S. Grimme, J. Am. Chem. Soc. 2000, 122, 1717-1724;
9. b) S. Grimme, J. Harren, A. Sobanski, F. Vogtle, Eur. J. Org. Chem. 1998, 1491-1509;
10. c) J. Autschbach, T. Ziegler, S. J. A. van Gisbergen, E. J. Baerends, J. Chem. Phys. 2002, 116, 6930-6940.
11. a) E. Botek, J.-M. Andŕ, B. Champagne, T. Verbiest, A. Persoons, J. Chem. Phys. 2005, 122, 234713;
12. b) W. N. Herman, Y. Kim, W. L. Cao, J. Goldhar, C. H. Lee, M. M. Green, V. Jain, M. J. Lee, J. Macromol. Sci. Part A 2003, 40, 1369-1982;
13. c) N. Takenaka, R. S. Sarangthem, B. Captain, Angew. Chem. 2008, 120, 9854-9856;
14. Angew. Chem. Int. Ed. 2008, 47, 9708-9710;
15. d) D. J. Weix, S. D. Dreher, T. J. Katz, J. Am. Chem. Soc. 2000, 122, 10027-10032;
16. e) M. T. Reetz, E. W. Beuttenmüller, R. Goddard, Tetrahedron Lett. 1997, 38, 3211- 3214;
17. f) M. T. Reetz, S. Sostmann, J. Organomet. Chem. 2000, 603, 105-109;
18. g) M. Samal, J. Misek, I. G. Stara, I. Stary, Collect. Czech. Chem. Commun. 2009, 74, 1151-1159;
19. h) A. Bossi, E. Licandro, S. Maiorana, C. Rigamonti, S. Righetto, G. R. Stephenson, M. Spassova, E. Botek, B. Champagne, J. Phys. Chem. C 2008, 112, 7900-7907.
20. a) K. Schmidt, S. Brovelli, V. Coropceanu, D. Beljonne, J. Cornil, C. Bazzini, T. Caronna, R. Tubino, F. Meinardi, Z. Shuai, J. L. Brédas, J. Phys. Chem. A 2007, 111, 10490-10499;
21. b) K. Schmidt, S. Brovelli, V. Coropceanu, J. L. Brédas, C. Bazzini, T. Caronna, R. Tubino, F. Meinardi, J. Phys. Chem. A 2006, 110, 11018-11024;
22. c) M. Sapir, E. Vander Donckt, Chem. Phys. Lett. 1975, 36, 108-110;
23. d) J. B. Birks, D. J. S. Birch, E. Cordemans, E. Vander Donckt, Chem. Phys. Lett. 1976, 43, 33-36;
24. e) O. E. Weigang, Jr. , J. A. Turner, P. A. Trouard, J. Chem. Phys. 1966, 45, 1126-1134;
25. f) Y. H. Tian, G. Park, M. Kertesz, Chem. Mater. 2008, 20, 3266-3277;
26. g) M. T. Reetz, S. Sostmann, Tetrahedron 2001, 57, 2515-2520.
27. a) C. Nuckolls, R. F. Shao, W. G. Jang, N. A. Clark, D. M. Walba, T. J. Katz, Chem. Mater. 2002, 14, 773-776;
28. b) A. J. Lovinger, C. Nuckolls, T. J. Katz, J. Am. Chem. Soc. 1998, 120, 264-268.
29. a) M. Miyasaka, A. Rajca, M. Pink, S. Rajca, J. Am. Chem. Soc. 2005, 127, 13806-13807;
30. b) J. Misek, F. Teply, I. G. Stara, M. Tichy, D. Saman, I. Cisarova, P. Vojtisek, I. Stary, Angew. Chem. 2008, 120, 3232-3235;
31. Angew. Chem. Int. Ed. 2008, 47, 3188-3191;
32. c) D. C. Harrowven, I. L. Guy, L. Nanson, Angew. Chem. 2006, 118, 2300- 2303;
33. Angew. Chem. Int. Ed. 2006, 45, 2242-2245;
34. d) E. Murguly, R. McDonald, N. R. Branda, Org. Lett. 2000, 2, 3169-3172;
35. e) J. Ichikawa, M. Yokota, T. Kudo, S. Umezaki, Angew. Chem. 2008, 120, 4948-4951;
36. Angew. Chem. Int. Ed. 2008, 47, 4870-4873;
37. f) T. Rasmusson, L. J. P. Martyn, G. Chen, A. Lough, M. Oh, A. K. Yudin, Angew. Chem. 2008, 120, 7117-7120;
38. Angew. Chem. Int. Ed. 2008, 47, 7009-7012;
39. g) B. Laleu, P. Mobian, C. Herse, B. W. Laursen, G. Hopfgartner, G. Bernardinelli, J. Lacour, Angew. Chem. 2005, 117, 1913-1917;
40. Angew. Chem. Int. Ed. 2005, 44, 1879-1883.
41. a) J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, VCH, Weinheim, 1995;
42. b) J. P. Sauvage, Transition Metals in Supramolecular Chemistry, Wiley, New York, 1994.
43. a) K. Sénéchal-David, A. Hemeryck, N. Tancrez, L. Toupet, J. A. G. Williams, I. Ledoux, J. Zyss, A. Boucekkine, J. P. Guegan, H. Le Bozec, O. Maury, J. Am. Chem. Soc. 2006, 128, 12243-12255;
44. b) T. Le Bouder, O. Maury, A. Bondon, K. Costuas, E. Amouyal, I. Ledoux, J. Zyss, H. Le Bozec, J. Am. Chem. Soc. 2003, 125, 12284- 12299;
45. c) O. Maury, H. Le Bozec, Acc. Chem. Res. 2005, 38, 691-704.
46. a) C. M. Hartshorn, P. J. Steel, Inorg. Chem. 1996, 35, 6902-6903;
47. b) M. Munakata, G. L. Ning, Y. Suenaga, T. Kurodo-Sowa, M. Maekawa, T. Ohta, Angew. Chem. 2000, 112, 4729-4731;
48. Angew. Chem. Int. Ed. 2000, 39, 4555-4557;
49. c) M. Yoshizawa, J. Nakagawa, K. Kumazawa, M. Nagao, M. Kawano, T. Ozeki, M. Fujita, Angew. Chem. 2005, 117, 1844-1847;
50. Angew. Chem. Int. Ed. 2005, 44, 1810-1813;
51. d) Q. Chu, D. C. Swenson, L. R. MacGillivray Angew. Chem. 2005, 117, 3635-3638;
52. Angew. Chem. Int. Ed. 2005, 44, 3569-3572;
53. Angew. Chem. Int. Ed. 2005, 44, 3569-3572.
54. a) G. Rapenne, C. Dietrich-Buchecker, J. P. Sauvage, J. Am. Chem. Soc. 1996, 118, 10932-10933;
55. b) C. J. Meskers, H. P. J. M. Dekkers, G. Rapenne, J. P. Sauvage, Chem. Eur. J. 2000, 6, 2129-2134.
56. a) A. Sudhakar, T. J. Katz, J. Am. Chem. Soc. 1986, 108, 179-181;
57. b) A. Sudhakar, T. J. Katz, B. W. Yang, J. Am. Chem. Soc. 1986, 108, 2790-2791;
58. c) F. Pammer, Y. Sun, M. Pagels, D. Weismann, H. Sitz- mann, W. R. Thiel, Angew. Chem. 2008, 120, 3315-3318;
59. Angew. Chem. Int. Ed. 2008, 47, 3271-3274;
60. d) T. J. Katz, A. Sudhakar, M. F. Teasley, A. M. Gilbert, W. E. Geiger, M. P. Robben, M. Wuensch, M. D. Ward, J. Am. Chem. Soc. 1993, 115, 3182-3198;
61. e) A. M. Gilbert, T. J. Katz, W. E. Geiger, M. P. Robben, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3199-3211;
62. f) Z. Gomez- Sandoval, E. Pena, C. Fonseca Guerra, F. M. Bickelhaupt, M. A. Mendez-Rojas, G. Merino, Inorg. Chem. 2009, 48, 2714-2716;
63. g) R. El-Abed, F. Aloui, J.-P. Genet, B. Ben-Hassine, A. Marinetti, J. Organomet. Chem. 2007, 692, 1156-1160;
64. h) M. H. Garcia, P. Florindo, M. F. M. Piedade, M. T. Duarte, Polyhedron 2009, 28, 621-629.
65. a) S. Graule, M. Rudolph, N. Vanthuyne, J. Autschbach, C. Roussel, J. Crassous, R. Réau, J. Am. Chem. Soc. 2009, 131, 3183-3185;
66. b) W. Shen, S. Graule, J. Crassous, C. Lescop, H. Gornitzka, R. Réau, Chem. Commun. 2008, 850-852;
67. c) L. Norel, M. Rudolph, N. Vanthuyne, J. A. G. Williams, C. Lescop, C. Roussel, J. Auchtsbach, J. Crassous, R. Réau, Angew. Chem. Int. Ed. 2010, 49, 99-102.
68. a) U. Knof, A. von Zelewsky, Angew. Chem. 1999, 111, 312-333;
69. Angew. Chem. Int. Ed. 1999, 38, 302-322;
70. b) H. Brunner, Angew. Chem. 1999, 111, 1248;
71. Angew. Chem. Int. Ed. 1999, 38, 1194;
72. c) J. Crassous, Chem. Soc. Rev. 2009, 38, 830-845;
73. d) A. Amouri, M. Gruselle, Chirality in Transition Metal Chemistry: Molecules, Supramolecular Assemblies and Materials, Wiley-VCH, Weinheim, 2009;
74. e) D. Amabilino, Chirality at the Nanoscale: Nanoparticles, Surfaces, Materials and More, Wiley-VCH, Weinheim, 2009.
75. a) P. Braunstein, J. Organomet. Chem. 2004, 689, 3953-3967;
76. b) R. G. Pearson, Inorg. Chem. 1973, 12, 712-713;
77. c) O. Mamula, A. von Zelewsky, J. Chem. Soc. Dalton Trans. 2001, 219-231;
78. d) J. N. Harvey, K. M. Heslop, A. G. Orpen, P. G. Pringle, Chem. Commun. 2003, 278-279.
79. a) R. Réau, P. Dyer, Comprehensive Heterocyclic Chemistry, Elsevier, Oxford, 2008;
80. b) F. Mathey, Phosphorus-carbon Heterocyclic Chemistry: The Rise of a New Domain, Elsevier, Oxford, 2001;
81. c) F. Mathey, Angew. Chem. 2003, 115, 1616-1643;
82. Angew. Chem. Int. Ed. 2003, 42, 1578-1604;
83. d) T. Baumgartner, R. Réau, Chem. Rev. 2006, 106, 4681-4727.
84. M. K. Cyrañski, T. M. Krygowski, A. R. Katritzky, P. von R. Schleyer, J. Org. Chem. 2002, 67, 1333-1338.
85. a) H.-C. Su, O. Fadhel, C.-J. Yang, T.-Y. Cho, C. Fave, M. Hissler, C.-C. Wu, R. Réau, J. Am. Chem. Soc. 2006, 128, 983-995;
86. b) M. Sebastian, M. Hissler, C. Fave, J. Rault-Berthelot, C. Odin, R. Réau, Angew. Chem. 2006, 118, 6298-6301;
87. Angew. Chem. Int. Ed. 2006, 45, 6152-6155;
88. c) V. Lemau de Talancé, M. Hissler, L.-Z. Zhang, ; T. Kárpáti, L. Nyulászi, D. Caras-Quintero, P. Bäuerle, R. Réau, Chem. Commun. 2008, 2200-2202;
89. d) Y. Matano, T. Miyajima, T. Fukushima, H. Kaji, Y. Kimura, H. Imahori, Chem. Eur. J. 2008, 14, 8102-8115;
90. e) Y. Matano, T. Miyajima, H. Imahori, Y. Kimura, J. Org. Chem. 2007, 72, 6200-6205;
91. f) Y. Dienes, S. Durben, T. Karpati, T. Neumann, U. Englert, L. Nyulaszi, T. Baumgartner, Chem. Eur. J. 2007, 13, 7487-7500;
92. g) A. Fukazawa, M. Hara, T. Okamoto, E.-C. Son, C. Xu, K. Tamao, S. Yamaguchi, Org. Lett. 2008, 10, 913- 916;
93. h) A. Fukazawa, H. Yamada, S. Yamaguchi, Angew. Chem. 2008, 120, 5664-5667;
94. Angew. Chem. Int. Ed. 2008, 47, 5582-5585;
95. i) H. T. Ngoc Huy, D. Donnadieu, F. Mathey, A. Muller, K. Colby, C. J. Bardeen, Organometallics 2008, 27, 5521-5524;
96. j) C. Hay, M. Hissler, C. Fischmeister, J. Rault-Berthelot, L. Toupet, L. Nyulaszi, R. Réau, Chem. Eur. J. 2001, 7, 4222-4236.
97. a) P. J. Fagan, W. A. Nugent, J. C. Calabrese, J. Am. Chem. Soc. 1994, 116, 1880-1889;
98. b) P. J. Fagan, W. A. Nugent, J. Am. Chem. Soc. 1988, 110, 2310-2312.
99. L. B. Liu, B. W. Yang, T. J. Katz, M. K. Poindexter, J. Org. Chem. 1991, 56, 3769-3775.
100. a) J. Crassous, R. Réau, Dalton Trans. 2008, 6865-6876;
101. b) C. Fave, M. Hissler, K. Sénéchal, I. Ledoux, J. Zyss, R. Réau, Chem. Commun. 2002, 1674-1675;
102. c) M. Sauthier, F. Leca, L. Toupet, R. Réau, Organometallics 2002, 21, 1591-1602;
103. d) M. Sauthier, B. Le Guennic, V. Deborde, L. Toupet, J.-F. Halet, R. Réau, Angew. Chem. 2001, 113, 234;
104. Angew. Chem. Int. Ed. 2001, 40, 228;
105. e) F. Leca, M. Sauthier, V. Deborde, L. Toupet, R. Réau, Chem. Eur. J. 2003, 9, 3785-3795;
106. f) F. Leca, C. Lescop, E. Rodriguez, K. Costuas, J.-F. Halet, R. Réau, R. Angew. Chem. 2005, 117, 4436-4439;
107. Angew. Chem. Int. Ed. 2005, 44, 4362-4365;
108. Angew. Chem. Int. Ed. 2005, 44, 4362-4365;
109. g) B. Nohra, S. Graule, C. Lescop, R. Réau, J. Am. Chem. Soc. 2006, 128, 3520.
110. a) S. Grimme, Chem. Phys. Lett. 2001, 339, 380-388;
111. b) F. Furche, R. Ahlrichs, C. Wachsmann, E. Weber, A. Sobanski, F. Vögtle, S. Grimme, J. Am. Chem. Soc. 2000, 122, 1717-1724.
112. a) Turbomole, Version 5.7.1, Quantum Chemistry Group, University of Karlsruhe, Karlsruhe;
113. b) K. Eichkorn, O. Treutler, H. Öhm, M. Häser, R. Ahlrichs, Chem. Phys. Lett. 1995, 242, 652-660;
114. c) K. Eichkorn, F. Weigend, O. Treutler, R. Ahlrichs, Theor. Chem. Acc. 1997, 97, 119-124.
115. A. Schäfer, H. Horn, R. Alrichs, J. Chem. Phys. 1992, 97, 2571-2577.
116. a) P. A. M. Dirac, Proc. R. Soc. London Ser. A 1929, 123, 714-733;
117. b) J. C. Slater, Phys. Rev. 1951, 81, 385-390;
118. c) S. Vosko, L. Wilk, M. Nusair, Can. J. Phys. 1980, 58, 1200-1211;
119. d) A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100;
120. e) J. P. Perdew, Phys. Rev. B 1986, 77, 3865-3868.
121. A. D. Becke, J. Chem. Phys. 1992, 96-97, 5648.
122. A. Klamt, G. Schüürmann, J. Chem. Soc. Perkin Trans. 2 1993, 799-805.
123. NBO 5.0, http://www.chem.wisc.edu/~nbo5/, E. D. Glendening, J. K. Badenhoop, A. E. Reed, J. E. Carpenter, J. A. Bohmann, C. M. Morales, F. Weinhold, Theoretical Chemistry Institute, University of Wisconsin, Madison, 2001.
124. Gaussian 03, Revision C.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford, CT, 2004.
125. "Natural Bond Orbital Methods": F. Weinhold, in Encyclopedia of Computational Chemistry (Ed.: P. von R. Schleyer), Wiley, New York, 1998, pp. 1792-1811.
126. a) J. Autschbach, T. Ziegler, J. Chem. Phys. 2002, 116, 891-896;
127. b) J. Autschbach, T. Ziegler, S. J. A. van Gisbergen, E. J. Baerends, J. Chem. Phys. 2002, 116, 6930-6940;
128. c) J. Autschbach, T. Ziegler, S. Patchkovskii, S. J. A. van Gisbergen, E. J. Baerends, J. Chem. Phys. 2002, 117, 581-592.
129. "Time-dependent Density Functional Response Theory for Molecules": M. E. Casida in Recent Advances in Density Functional Methods, Vol.1, World Scientific, Singapore, 1995, pp. 155-192.
130. R. Bauernschmitt, R. Ahlrichs, Chem. Phys. Lett. 1996, 256, 454-464.
131. A. D. McLachlan, M. A. Ball, Rev. Mod. Phys. 1964, 36, 844-855.
132. a) S. F. Boys, J. M. Foster, Rev. Mod. Phys. 1960, 32, 300-302;
133. b) C. Edmiston, K. Ruedenberg, Rev. Mod. Phys. 1963, 35, 457-465;
134. c) W. von Niessen, J. Chem. Phys. 1972, 56, 4290-4297;
135. d) J. Pipek, P. G. Mezey, J. Chem. Phys. 1989, 90, 4916-4926.
136. A. Schäfer, C. Huber, R. Alrichs, J. Chem. Phys. 1994, 100, 5829-5835.
137. When not specified 5c1 corresponds to (P,SP)-s-trans configuration.
138. I. J. Tinoco, R. W. Woody, J. Chem. Phys. 1964, 40, 160-165.
139. a) O. Mamula, A. von Zelewsky, J. Chem. Soc. Dalton Trans. 2000, 3, 219-231;
140. b) J. N. Harvey, K. M. Heslop, A. G. Orpen, P. G. Pringle, Chem. Commun. 2003, 278-279.
141. J. Autschbach, Chirality 2010, in press.
142. a) L. D. Quin, J. P. Gratz, T. P. Barket, J. Org. Chem. 1968, 33, 1034- 1041;
143. b) D. A. Lightner, D. T. Hefelfinger, T. W. Powers, G. W. Frank, K. N. Trueblood, J. Am. Chem. Soc. 1972, 94, 3492-3497.
144. Z. Otwinowski, W. Minor in Methods in Enzymology (Eds.: C. W. Carter, Jr., R. M. Sweet), Academic Press, New York, 1997, p. 307.
145. A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Cryst. 1999, 32, 115.
146. SHELX97, Program for the refinement of crystal structures, G. M. Sheldrick, University of Göttingen, Göttingen, 1997.
147. International Tables for X-ray Crystallography, Vol.C, Kluwer, Dordrech, 1992.