Synthesis and spectroscopic investigation of aggregation through cooperative π-π and C-H⋯O interactions in a novel pyrene octaaldehyde derivative

Organic Letters

Volumn 8, Issue 13, 2006, Pages 2739-2742

  Venkataramana, Gandikota ^a   Sankararaman, Sethuraman ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746115759     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060767h     Document Type: Article

References (36)

1. (a) Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: Oxford, 1999.
2. (b) Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; VCH: Weinheim, 1995.
3. (c) Müller-Dethlefs, K.; Hobza, P. Chem. Rev. 2000, 100, 143-167.
4. (a) Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elseiver: Amsterdam, 1989; Chapter 5, pp 115-165.
5. (b) Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991.
6. (c) Scheiner, S. Hydrogen Bonding: A Theoretical Perspective; Oxford University Press: Oxford, 1997.
7. (d) For H-bonding interactions in globular proteins, see: Baker, E. N.; Hubbard, R. E. Prog. Biophys. Mol. Biol. 1984, 44, 97-197.
8. (a) Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891-4945.
9. (b) Watson, M. D.; Fechtenkötter, A.; Müllen, K. Chem. Rev. 2001, 101, 1267-1300.
10. (c) Sokolov, A. N.; Friscic, T.; MacGillivray, L. R. J. Am. Chem. Soc. 2006, 128, 2806-2807.
11. (d) Claessens, C. G.; Stoddart, J. F. J. Phys. Org. Chem. 1997, 10, 254-272.
12. (a) Moorthy, J. N.; Natarajan, R.; Venugopalan, P. J. Mol. Struct. 2005, 741, 107-114.
13. (b) Moorthy, J. N.; Natarajan, R.; Mal, P.; Venugopalan, P. J. Am. Chem. Soc. 2002, 124, 6530-6531.
14. (c) Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311-2327.
15. (a) Egli, M.; Gessner, R. V. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 180-184.
16. (b) Berger, I.; Egli, M.; Rich, A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 12116-12121.
17. (c) Ornstein, R. L.; Zheng, Y. J. J. Biomol. Struct. Dyn. 1997, 14, 657-665.
18. (d) Takahara, P. M.; Frederick, C. A.; Lippard, S. J. J. Am. Chem. Soc. 1996, 118, 12309-12321.
19. Jiang, L.; Lai, L. J. Biol. Chem. 2002, 277, 37732-37740.
20. Narayanan, V.; Sankararaman, S.; Hopf, H. Eur. J. Org. Chem. 2005, 2740-2746.
21. Venkataramana, G.; Sankararaman, S. Eur. J. Org. Chem. 2005, 4162-4166.
22. For the effect of concentration on the color and absorption spectrum of perylene biamide dyes, see: (a) Würthner, F. Chem. Commun. 2004, 1564-1579.
23. (b) Würthner, F.; Thalacker, C.; Diele, S.; Tschierske, C. Chem.-Eur. J. 2001, 7, 2245-2253.
24. (a) Berlman, I. B. Handbook of Fluorescence Spectra of Aromatic Molecules; Academic Press: New York, 1965; p 173.
25. (b) Winnik, F. M. Chem. Rev. 1993, 93, 587-614.
26. For examples of π-stacking interactions in pyrene and excimer emission, see: (a) Vero, A.; Suzuki, I.; Osa, T. J. Am. Chem. Soc. 1989, 111, 6391-6397.
27. (b) Chou, T.-C.; Hwa, C.-L.; Lin, J.-J.; Liao, K.-C.; Tseng, J.-C. J. Org. Chem. 2005, 70, 9717-9726.
28. (c) Yuasa, H.; Miyagawa, N.; Izumi, T.; Nakatani, M.; Izumi, M.; Hashimoto, H. Org. Lett. 2004, 6, 1489-1492.
29. (d) Nishizawa, S.; Kaot, Y.; Teramae, N. J. Am. Chem. Soc. 1999, 121, 9463-9464.
30. (e) Lee, S. H.; Kim, S. H.; Kim, S. K.; Jung, J. H.; Kim, J. S. J. Org. Chem. 2005, 70, 9288-9295.
31. Yang, S.-W.; Elangovan, A.; Hwang, K.-C.; Ho, T.-I. J. Phys. Chem. B 2005, 109, 16628-16635.
32. For π-stacking of acenes bearing bulky peripheral substituents, see: Antony, J. E.; Brooks, J. S.; Eaton, D. L.; Perkin, S. R. J. Am. Chem. Soc. 2001, 123, 9482-9483.
33. Scheiner, S.; Kar, T.; Gu, Y. J. Biol. Chem. 2001, 276, 9832-9837.
34. For temperature-dependent NMR due to π-stacking and aggregation, see: (a) Watson, M. D.; Jäckel, F.; Severin, N.; Rabe, J. P.; Müllen, K. J. Am. Chem. Soc. 2004, 126, 1402-1407.
35. (b) Fechtenkötter, A.; Saalwächter, K.; Harbison, M. A.; Müllen, K.; Spiess, H. W. Angew. Chem., Int. Ed. 1999, 38, 3039-3042.
36. (c) Shetty, A. S.; Fischer, P. R.; Storck, K. F.; Bohn, P. W.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 9409-9414.