Solid-state photopolymerization of a shape-persistent macrocycle with two 1,8-diazaanthracene units in a single crystal

Journal of the American Chemical Society

Volumn 134, Issue 28, 2012, Pages 11721-11725

  Li, Ming ^a   Schlüter, A Dieter ^a   Sakamoto, Junji ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

COUNTERIONS; CYCLOADDITION REACTION; MACROCYCLES; MACROCYCLICS; PROTONATED; RIGID-ROD POLYMERS; SPATIAL POSITIONING; STRUCTURAL CHANGE;

CYCLOADDITION; ORGANIC SOLVENTS; PHOTOPOLYMERIZATION; SINGLE CRYSTALS; SURFACE ACTIVE AGENTS;

MONOMERS;

ANTHRACENE; MACROCYCLIC COMPOUND; MONOMER; POLYMER; SOLVENT;

ARTICLE; ATOMIC FORCE MICROSCOPY; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL; CRYSTAL STRUCTURE; CYCLOADDITION; DEPOLYMERIZATION; DIMERIZATION; POLYMERIZATION; SYNTHESIS; TEMPERATURE;

EID: 84863896489     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3038905     Document Type: Article

References (44)

1. Schmidt, G. M. J. Solid State Photochemistry. Verlag Chemie, Weinheim, Germany, 1976.
2. Wegner, G. Z. Naturforsch. (b) 1969, 24, 824
3. Wegner, G. Pure Appl. Chem. 1977, 49, 443
4. Enkelmann, V. Adv. Polym. Sci. 1984, 63, 91
5. Selected, recent examples: Liu, D.; Ren, Z.-G.; Li, H.-X.; Lang, J.-P.; Li, N.-Y.; Abrahams, B. F. Angew. Chem., Int. Ed. 2010, 49, 4767
6. Itoh, T.; Suzuki, T.; Uno, T.; Kubo, M.; Tohnai, N.; Miyata, M. Angew. Chem., Int. Ed. 2011, 123, 2301
7. Zhu, L.; Agarwal, A.; Lai, J.; Al-Kaysi, R. O.; Tham, F. S.; Ghaddar, T.; Mueller, L.; Bardeen, C. J. J. Mater. Chem. 2011, 21, 6258
8. For an example in which a less complex but sensitive compound is generated, see: Legrand, Y.-M.; Lee, A. v. d.; Barboiu, M. Science 2010, 329, 299
9. For a recent elegant study on thermally induced diacetylene polymerization in a single crystal, see: Hsu, T.-J.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 2012, 134, 142
10. Novak, K.; Enkelmann, V.; Wegner, G.; Wagener, K. B. Angew. Chem., Int. Ed. 1993, 32, 1614
11. Novak, K.; Enkelmann, V.; Wegner, G.; Wagener, K. B. J. Am. Chem. Soc. 1993, 115, 10390
12. Kissel, P.; Erni, R.; Schweizer, W. B.; Rossell, M. D.; King, B. T.; Bauer, T.; Götzinger, S.; Schlüter, A. D.; Sakamoto, J. Nature Chem. 2012, 4, 287
13. Becker, H.-D. Chem. Rev. 1993, 93, 145
14. Bouas-Laurent, H.; Desvergne, J.-P.; Castellan, A.; Lapouyade, R. Chem. Soc. Rev. 2000, 29, 43
15. Bouas-Laurent, H.; Desvergne, J.-P.; Castellan, A.; Lapouyade, R. Chem. Soc. Rev. 2001, 30, 248
16. For main chain scission resists, for example, see: Reichmanis, E.; Novembre, A. E. Annu. Rev. Mater. Sci. 1993, 23, 11
17. Zouev, I.; Cao, D.-K.; Sreevidya, T. V.; Telzhensky, M.; Botoshansky, M.; Kaftory, M. Cryst. Eng. Commun. 2011, 13, 4376
18. Also, see: Ito, Y.; Olovsson, G. J. Chem. Soc., Perkin Trans. 1 1997, 127
19. Ito, Y.; Fujita, H. J. Org. Chem. 1996, 61, 5677
20. For example, see: Jouvenot, D.; Glaser, E. C.; Tor, Y. Org. Lett. 2006, 8, 1987
21. Berni, A.; Dolain, C.; Kauffmann, B.; Léger, J.-M.; Zhan, C.; Huc, I. J. Org. Chem. 2008, 73, 2687
22. Yamada, S.; Kawamura, C. Org. Lett. 2012, 14, 1572
23. For other methods of enforcing ftf-packing, see: Ihmels, H.; Leusser, D.; Pfeiffer, M.; Stalke, D. Tetrahedron 2000, 56, 6867
24. Horiguchi, M.; Ito, Y. J. Org. Chem. 2006, 71, 3608
25. Itoh, T.; Suzuki, T.; Uno, T.; Kubo, M.; Tohnai, N.; Miyata, M. Angew. Chem., Int. Ed. 2011, 123, 2301 and references cited therein.
26. For related all-hydrocarbon cycles, see: Toyota, S.; Goichi, M.; Kotani, M. Angew. Chem., Int. Ed. 2004, 43, 2248
27. Zimmerman, S. C.; Saionz, K. W.; Zheng, Z. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 1190
28. Tu, S.; Li, T.; Shi, F.; Fang, F.; Zhu, S.; Wei, X.; Zong, Z. Chem. Lett. 2005, 34, 732
29. Mahamoud, A.; Galy, J. P.; Barbe, J. Org. React. Proc. Int. 1994, 26, 473
30. Kissel, P.; van Heijst, J.; Enning, R.; Stemmer, A.; Schlüter, A. D.; Sakamoto J. Org. Lett. 2010, 12, 2778
31. Saha, A.; van Heijst, J.; Sakamoto, J.; Schlüter, A. D. Synlett 2012, 23, 1467
32. An investigation of packing effects on the photochemical crystal-to-crystal transformation will be independently reported: Li, M.; Schlüter, A. D.; Sakamoto, J. In preparation.
33. Sakamoto, J.; van Heijst, J.; Lukin, O.; Schlüter, A. D. Angew. Chem., Int. Ed. 2009, 48, 1030
34. Kissel, P.; Schlüter, A. D.; Sakamoto, J. Chem.-Eur. J. 2009, 15, 8955
35. This shift is significantly lower than that of the parent anthracene dimer which finds its explanation by a through-space effect of the two nearby nitrogen atoms and the fact that all nitrogens are protonated in the solvent TFA. Similar through space effects in rigid compounds have been described: Zoch, H. G.; Schlüter, A. D.; Szeimies, G. Tetrahedron Lett. 1981, 22, 3835
36. Cao, Y.; Smith, P.; Heeger, A. J. Synth. Met. 1992, 48, 91
37. Kurth, D. G.; Severin, N.; Rabe, J. P. Angew. Chem., Int. Ed. 2002, 41, 3681
38. Rabe, J. P.; Buchholz, S. Science 1991, 253, 424
39. Rabe, J. P.; Buchholz, S. Phys. Rev. Lett. 1991, 66, 2096
40. For epitaxial effects exerted on (thick) dendronized polymers, see: Stocker, W.; Schürmann, B. L.; Rabe, J. P.; Förster, S.; Lindner, P.; Neubert, I.; Schlüter, A. D. Adv. Mater. 1998, 10, 793
41. van Noort, S. J. T.; van der Werf, K. O.; de Grooth, B. G.; Van Hulst, N. F.; Greve, J. Ultramicroscopy 1997, 69, 117
42. Zhuang, W.; Ecker, C.; Metselaar, G. A.; Rowan, A. E.; Nolte, R. J. M.; Samorí, P.; Rabe, J. P. Macromolecules 2005, 38, 473
43. Zhang, B.; Wepf, R.; Fischer, K.; Schmidt, M.; Besse, S.; Lindner, P.; King, B. T.; Sigel, R.; Schurtenberger, P.; Talmon, Y.; Ding, Y.; Kröger, M.; Halperin, A.; Schlüter, A. D. Angew. Chem., Int. Ed. 2011, 50, 737
44. Zhang, B.; Wepf, R.; Kröger, M.; Halperin, A.; Schlüter, A. D. Macromolecules 2011, 44, 6785