Chimerical pyrene-based [7]helicenes as twisted polycondensed aromatics

Chemistry - A European Journal

Volumn 21, Issue 24, 2015, Pages 8910-8917

  Buchta, Michal ^a   Rybáček, Jiří ^a   Jančařík, Andrej ^a   Kudale, Amit A ^a   Buděšínský, Miloš ^a   Chocholoušová, Jana Vacek ^a   Vacek, Jaroslav ^a   Bednárová, Lucie ^a   Císařová, Ivana ^c   Bodwell, Graham J ^b   Starý, Ivo ^a   Stará, Irena G ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

^c CHARLES UNIVERSITY   (Czech Republic)

Author keywords

alkynes; asymmetric synthesis; chirality; cycloisomerisation; helical structures

Indexed keywords

CHIRALITY; COLUMN CHROMATOGRAPHY; DICHLOROMETHANE; DICHROISM; FLUORESCENCE; ISOMERIZATION; LIQUID CHROMATOGRAPHY; NICKEL; PYRENE; QUANTUM THEORY; SCAFFOLDS;

ALKYNES; ASYMMETRIC SYNTHESIS; CYCLOISOMERISATION; ELECTRONIC CIRCULAR DICHROISM; FLUORESCENCE SPECTRA; HELICAL STRUCTURES; PHYSICOCHEMICAL PROPERTY; X RAY CRYSTAL STRUCTURES;

CRYSTAL STRUCTURE;

EID: 84930210934     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201500826     Document Type: Article

References (106)

1. M. Gingras, Chem. Soc. Rev. 2013, 42, 968-1006
2. M. Gingras, G. Félix, R. Peresutti, Chem. Soc. Rev. 2013, 42, 1007-1050
3. M. Gingras, Chem. Soc. Rev. 2013, 42, 1051-1095
4. A. Urbano, M. C. Carreño, Org. Biomol. Chem. 2013, 11, 699-708
5. Y. Shen, C.-F. Chen, Chem. Rev. 2012, 112, 1463-1535
6. I. G. Stará, I. Starý, in Science of Synthesis, Vol. 45b (Eds:, J. S. Siegel, Y. Tobe,), Thieme, Stuttgart, 2010, pp. 885-953
7. F. Dumitrascu, D. G. Dumitrescu, I. Aron, ARKIVOC 2010, 2010 (i), 1-32
8. I. Starý, I. G. Stará, in Strained Hydrocarbons (Ed.:, H. Dodziuk,), Wiley-VCH, Weinheim, 2009, pp. 166-176
9. A. Rajca, M. Miyasaka, in Functional Organic Materials (Eds.:, T. J. J. Müller, U. H. F. Bunz,), Wiley-VCH, Weinheim, 2007, pp. 547-581
10. S. K. Collins, M. P. Vachon, Org. Biomol. Chem. 2006, 4, 2518-2524
11. A. Urbano, Angew. Chem. Int. Ed. 2003, 42, 3986-3989
12. Angew. Chem. 2003, 115, 4116-4119
13. K. Sato, S. Arai, in Cyclophane Chemistry for the 21st Century (Ed.:, H.Takemura,), Research Signpost, Trivandrum, 2002, pp. 173-197
14. H. Hopf, in Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives, Wiley-VCH, Weinheim, 2000, pp. 323-330
15. T. J. Katz, Angew. Chem. Int. Ed. 2000, 39, 1921-1923
16. Angew. Chem. 2000, 112, 1997-1999
17. F. Vögtle, in Fascinating Molecules in Organic Chemistry, Wiley, New York, 1992, pp. 156-180
18. G. Oremek, U. Seiffert, A. Janecka, Chem.-Ztg. 1987, 111, 69-75
19. K. P. Meurer, F. Vögtle, Top. Curr. Chem. 1985, 127, 1-76
20. W. H. Laarhoven, W. J. C. Prinsen, Top. Curr. Chem. 1984, 125, 63-130
21. R. H. Martin, Angew. Chem. Int. Ed. Engl. 1974, 13, 649-660
22. Angew. Chem. 1974, 86, 727-738
23. H. Wynberg, Acc. Chem. Res. 1971, 4, 65-73.
24. P. Sehnal, I. G. Stará, D. Šaman, M. Tich, J. Míšek, J. Cvačka, L. Rulíšek, J. Chocholoušová, J. Vacek, G. Goryl, M. Szymonski, I. Císařová, I. Starý, Proc. Natl. Acad. Sci. USA 2009, 106, 13169-13174
25. M. Miyasaka, A. Rajca, M. Pink, S. Rajca, J. Am. Chem. Soc. 2005, 127, 13806-13807
26. T. Caronna, R. Sinisi, M. Catellani, L. Malpezzi, S. V. Meille, A. Mele, Chem. Commun. 2000, 1139-1140
27. K. Yamada, S. Ogashiwa, H. Tanaka, H. Nakagawa, H. Kawazura, Chem. Lett. 1981, 343-346
28. H. Wynberg, M. B. Groen, J. Am. Chem. Soc. 1970, 92, 6664-6665.
29. A. Moradpour, H. Kagan, M. Baes, G. Morren, R. H. Martin, Tetrahedron 1975, 31, 2139-2143.
30. R. H. Martin, G. Morren, J. J. Schurter, Tetrahedron Lett. 1969, 10, 3683-3688
31. R. H. Martin, V. Libert, J. Chem. Res. 1980, 130-131.
32. R. H. Martin, M. Baes, Tetrahedron 1975, 31, 2135-2137.
33. S. Han, D. R. Anderson, A. D. Bond, H. V. Chu, R. L. Disch, D. Holmes, J. M. Schulman, S. J. Teat, K. P. C. Vollhardt, G. D. Whitener, Angew. Chem. Int. Ed. 2002, 41, 3227-3230
34. Angew. Chem. 2002, 114, 3361-3364.
35. J. Roose, S. Achermann, O. Dumele, F. Diederich, Eur. J. Org. Chem. 2013, 3223-3231
36. A. Sudhakar, T. J. Katz, B. W. Yang, J. Am. Chem. Soc. 1986, 108, 2790-2791.
37. F. Fenili, C. Rigamonti, A. Bossi, P. Ferruti, A. Manfredi, S. Maiorana, C. Baldoli, S. Cauteruccio, E. Licandro, E. Ranucci, J. Polym. Sci. Pol. Chem. 2010, 48, 4704-4710
38. T. Iwasaki, Y. Kohinata, H. Nishide, Org. Lett. 2005, 7, 755-758
39. T. P. Bender, Z. Y. Wang, J. Polym. Sci. Pol. Chem. 2000, 38, 3991-3996
40. Y. Dai, T. J. Katz, D. A. Nichols, Angew. Chem. Int. Ed. Engl. 1996, 35, 2109-2111
41. Angew. Chem. 1996, 108, 2230-2232.
42. L. Wang, P. L. Warburton, Z. Szekeres, P. Surjan, P. G. Mezey, J. Chem. Inf. Model. 2005, 45, 850-855.
43. A. Jančařík, J. Rybáček, K. Cocq, J. Vacek Chocholoušová, J. Vacek, R. Pohl, L. Bednárová, P. Fiedler, I. Císařová, I. G. Stará, I. Starý, Angew. Chem. Int. Ed. 2013, 52, 9970-9975
44. Angew. Chem. 2013, 125, 10154-10159
45. J. Seibel, O. Allemann, J. S. Siegel, K.-H. Ernst, J. Am. Chem. Soc. 2013, 135, 7434-7437
46. T. Hatakeyama, S. Hashimoto, T. Oba, M. Nakamura, J. Am. Chem. Soc. 2012, 134, 19600-19603
47. Y. Sawada, S. Furumi, A. Takai, M. Takeuchi, K. Noguchi, K. Tanaka, J. Am. Chem. Soc. 2012, 134, 4080-4083
48. A. Pradhan, P. Dechambenoit, H. Bock, F. Durola, Angew. Chem. Int. Ed. 2011, 50, 12582-12585
49. Angew. Chem. 2011, 123, 12790-12793
50. W. H. Laarhoven, R. J. F. Nivard, Tetrahedron 1976, 32, 2445-2450
51. W. H. Laarhoven, P. G. F. Boumans, Rec. Trav. Chim. Pays-Bas 1975, 94, 114-118
52. W. H. Laarhoven, T. J. H. M. Cuppen, R. J. F. Nivard, Rec. Trav. Chim. Pays-Bas 1968, 87, 687-698
53. A. Jenard-De Koninck, N. Defay, R. De Ridder, Bull. Soc. Chim. Belg. 1960, 69, 558-562.
54. A.-C. Bédard, A. Vlassova, A. C. Hernandez-Perez, A. Bessette, G. S. Hanan, M. A. Heuft, S. K. Collins, Chem. Eur. J. 2013, 19, 16295-16302
55. J.-Y. Hu, A. Paudel, N. Seto, X. Feng, M. Era, T. Matsumoto, J. Tanaka, M. R. J. Elsegood, C. Redshaw, T. Yamato, Org. Biomol. Chem. 2013, 11, 2186-2197
56. J.-Y. Hu, X. Feng, A. Paudel, H. Tomiyasu, U. Rayhan, P. Thuéry, M. R. J. Elsegood, C. Redshaw, T. Yamato, Eur. J. Org. Chem. 2013, 5829-5837
57. H. Bock, D. Subervie, P. Mathey, A. Pradhan, P. Sarkar, P. Dechambenoit, E. A. Hillard, F. Durola, Org. Lett. 2014, 16, 1546-1549
58. R. J. Hayward, A. C. Hopkinson, C. C. Leznoff, Tetrahedron 1972, 28, 439-447
59. F. A. Vingiello, P. D. Henson, J. Org. Chem. 1965, 30, 2842-2845.
60. S. Xiao, S. J. Kang, Y. Wu, S. Ahn, J. B. Kim, Y.-L. Loo, T. Siegrist, M. L. Steigerwald, H. Li, C. Nuckolls, Chem. Sci. 2013, 4, 2018-2023
61. K. Kawasumi, Q. Zhang, Y. Segawa, L. T. Scott, K. Itami, Nat. Chem. 2013, 5, 739-744
62. F. Schlütter, T. Nishiuchi, V. Enkelmann, K. Müllen, Angew. Chem. Int. Ed. 2014, 53, 1538-1542
63. Angew. Chem. 2014, 126, 1564-1568.
64. G. Treboux, P. Lapstun, Z. H. Wu, K. Silverbrook, Chem. Phys. Lett. 1999, 301, 493-497.
65. N. Takenaka, R. S. Sarangthem, B. Captain, Angew. Chem. Int. Ed. 2008, 47, 9708-9710
66. Angew. Chem. 2008, 120, 9854-9856; in enantioselective propargylation of aldehydes
67. J. Chen, B. Captain, N. Takenaka, Org. Lett. 2011, 13, 1654-1657; in acid-catalysed asymmetric Friedel-Crafts reaction
68. N. Takenaka, J. Chen, B. Captain, R. S. Sarangthem, A. Chandrakumar, J. Am. Chem. Soc. 2010, 132, 4536-4537.
69. J. Rybáček, G. Huerta-Angeles, A. Kollárovič, I. G. Stará, I. Starý, P. Rahe, M. Nimmrich, A. Kühnle, Eur. J. Org. Chem. 2011, 853-860
70. F. Teplý, I. G. Stará, I. Starý, A. Kollárovič, D. Luštinec, Z. Krausová, D. Šaman, P. Fiedler, Eur. J. Org. Chem. 2007, 4244-4250
71. F. Teplý, I. G. Stará, I. Starý, A. Kollárovič, D. Šaman, Š. Vyskočil, P. Fiedler, J. Org. Chem. 2003, 68, 5193-5197
72. F. Teplý, I. G. Stará, I. Starý, A. Kollárovič, D. Šaman, L. Rulíšek, P. Fiedler, J. Am. Chem. Soc. 2002, 124, 9175-9180.
73. T. Shibata, T. Uchiyama, Y. Yoshinami, S. Takayasu, K. Tsuchikama, K. Endo, Chem. Commun. 2012, 48, 1311-1313
74. O. Songis, J. Míšek, M. B. Schmid, A. Kollárovič, I. G. Stará, D. Šaman, I. Císařová, I. Starý, J. Org. Chem. 2010, 75, 6889-6899
75. K. Tanaka, N. Fukawa, T. Suda, K. Noguchi, Angew. Chem. Int. Ed. 2009, 48, 5470-5473
76. Angew. Chem. 2009, 121, 5578-5581
77. J. Míšek, F. Teplý, I. G. Stará, M. Tichý, D. Šaman, I. Císařová, P. Vojtíšek, I. Starý, Angew. Chem. Int. Ed. 2008, 47, 3188-3191
78. Angew. Chem. 2008, 120, 3232-3235
79. K. Tanaka, A. Kamisawa, T. Suda, K. Noguchi, M. Hirano, J. Am. Chem. Soc. 2007, 129, 12078-12079.
80. J. Žádný, A. Jančařík, A. Andronova, M. Šámal, J. Vacek Chocholoušová, J. Vacek, R. Pohl, D. Šaman, I. Císařová, I. G. Stará, I. Starý, Angew. Chem. Int. Ed. 2012, 51, 5857-5861
81. Angew. Chem. 2012, 124, 5959-5963
82. M. R. Crittall, H. S. Rzepa, D. R. Carbery, Org. Lett. 2011, 13, 1250-1253
83. P. Sehnal, Z. Krausová, F. Teplý, I. G. Stará, I. Starý, L. Rulíšek, D. Šaman, I. Císařová, J. Org. Chem. 2008, 73, 2074-2082
84. I. G. Stará, Z. Alexandrová, F. Teplý, P. Sehnal, I. Starý, D. Šaman, M. Buděšínský, J. Cvačka, Org. Lett. 2005, 7, 2547-2550.
85. L. Adriaenssens, L. Severa, D. Koval, I. Císařová, M. Martínez Belmonte, E. C. Escudero-Adán, P. Novotná, P. Sázelová, J. Vávra, R. Pohl, D. Šaman, M. Urbanová, V. Kašička, F. Teplý, Chem. Sci. 2011, 2, 2314-2320 and references cited therein.
86. N. J. Turro, V. Ramamurthy, J. C. Scaiano, in Modern Molecular Photochemistry of Organic Molecules, University Science Books, Sausalito, 2010, pp. 253-255
87. T. Föster, K. Z. Kasper, Electrochem. 1955, 59, 976-982.
88. A. G. Crawford, Z. Liu, I. A. I. Mkhalid, M.-H. Thibault, N. Schwarz, G. Alcaraz, A. Steffen, J. C. Collings, A. S. Batsanov, J. A. K. Howard, T. B. Marder, Chem. Eur. J. 2012, 18, 5022-5035.
89. B. Felber, F. Diederich, Helv. Chim. Acta 2005, 88, 120-153.
90. R. H. Martin, M. J. Marchant, Tetrahedron 1974, 30, 343-345.
91. R. H. Martin, M. J. Marchant, Tetrahedron 1974, 30, 347-349.
92. J. Vacek Chocholoušová, J. Vacek, A. Andronova, J. Míšek, O. Songis, M. Šámal, I. G. Stará, M. Meyer, M. Bourdillon, L. Pospíšil, I. Starý, Chem. Eur. J. 2014, 20, 877-893.
93. B. Heller, M. Hapke, C. Fischer, A. Andronova, I. Starý, I. G. Stará, J. Organomet. Chem. 2013, 723, 98-102
94. I. G. Stará, A. Andronova, A. Kollárovič, Š. Vyskočil, S. Jugé, G. C. Lloyd-Jones, P. J. Guiry, I. Starý, Collect. Czech. Chem. Commun. 2011, 76, 2005-2022.
95. A. Geny, N. Agenet, L. Iannazzo, M. Malacria, C. Aubert, V. Gandon, Angew. Chem. Int. Ed. 2009, 48, 1810-1813
96. Angew. Chem. 2009, 121, 1842-1845.
97. Crystallographic data (excluding structure factors) for (M,R,R)-(-)- 2 have been deposited with the Cambridge Crystallographic Data Centre. CCDC 973162 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
98. M. Joly, N. Defay, R. H. Martin, J. P. Declercq, G. Germain, B. Soubrier-Payen, M. van Meerssche, Helv. Chim. Acta 1977, 60, 537-560
99. T. E. M. van den Hark, P. T. Beurskens, Cryst. Struct. Commun. 1976, 5, 247-251
100. P. T. Beurskens, G. Beurskens, T. E. M. van den Hark, Cryst. Struct. Commun. 1976, 5, 241-246.
101. DFT calculations tend to significantly underestimate the intramolecular stabilisation:, L. Rulíšek, O. Exner, L. Cwiklik, P. Jungwirth, I. Starý, L. Pospíšil, Z. Havlas, J. Phys. Chem. C 2007, 111, 14948-14955.
102. S. Grimme, J. Comput. Chem. 2006, 27, 1787-1799.
103. Y. Niko, S. Kawauchi, S. Otsu, K. Tokumaru, G. Konishi, J. Org. Chem. 2013, 78, 3196-3207.
104. Emission λmax of the pyrene excimer in cyclohexanol (10-2 M):, J. M. G. Martinho, J. P. Farinha, M. N. Berberan-Santos, J. Duhamel, M. A. Winnik, J. Chem. Phys. 1992, 96, 8143-8149.
105. H. A. Staab, N. Riegler, F. Diederich, C. Krieger, D. Schweitzer, Chem. Ber. 1984, 117, 246-259.
106. F. M. Winnik, Chem. Rev. 1993, 93, 587-614.