Conformational isomers from rotation of diacetylenic bond in an ethynylpyrene-substituted molecular hinge

Journal of Organic Chemistry

Volumn 73, Issue 6, 2008, Pages 2404-2407

  Sankararaman, Sethuraman ^a   Venkataramana, Gandikota ^a   Varghese, Babu ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

DIACETYLENIC BOND; ROOM TEMPERATURE;

CHEMICAL BONDS; FLUORESCENCE SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

ISOMERS;

ETHYNYLPYRENE; PYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; FLUORESCENCE SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; X RAY CRYSTALLOGRAPHY;

EID: 41849135454     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7024724     Document Type: Article

References (34)

1. (a) Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891-4945.
2. (b) Hoeben, F. J. M.; Jonkheijm, P.; Meijer, E. W.; Schenning, A. P. H. J. Chem. Rev. 2005, 105, 1491-1546.
3. (c) Watson, M. D.; Jäckel, F.; Severin. N.; Rabe. J. P.; Mullen, K. J. Am. Chem. Soc. 2004, 126, 1402-1407.
4. (d) Sokolov, A. N.; Friscic, T.; MacGillivray, R. J. Am. Chem. Soc. 2006, 128, 2806-2807.
5. (e) Dickey, K. C.; Anthony, J. E.; Loo, Y.-L. Adv. Mater. 2006, 18, 1721-1726.
6. (f) Payne, M. M.; Parkin, S. R.; Anthony, J. E. J. Am. Chem. Soc. 2005, 127, 8028-8029.
7. Winnik, F. M. Chem. Rev. 1993, 93, 587.
8. For recent sensor applications, see: (a) Suzuki, I.; Ui, M.; Yamauchi, A. J. Am. Chem. Soc. 2006, 128, 4498-4499.
9. (b) Schazmann, B.; Alhashimy, N.; Diamond, D. J. Am. Chem. Soc. 2006, 128, 8607-8614.
10. (c) Choi, J. K.; Kim, S. H.; Yoon, J.; Lee, K.-H.; Bartsch, R. A.; Kim, J. S. J. Org. Chem. 2006, 71, 8011-8015 and refs 11, 13, and 14 cited therein.
11. (d) Dale, T. J.; Rabek, J., Jr. J. Am. Chem. Soc. 2006, 128, 4500-4501.
12. For electronics and photonics applications, see: (e) Zhang, H.; Wang, Y.; Shao, K.; Lin, Y.; Chen, S.; Qiu, W.; Sun, X.; Qi, T.; Ma, Y.; Yu, G.; Su, Z.; Zhu, D. Chem. Commun. 2006, 755-757.
13. (f) Jia, W.-L.; McCormick, T.; Lin, Q.-D.; Fukutani, H.; Motala, M.; Wang, R.-Y.; Tao, Y.; Wang, S. J. Mater. Chem. 2004, 14, 3344-3350.
14. (g) Ogino, K.; Iwashima, S.; Inokuchi, H.; Harada, Y. Bull. Chem. Soc. Jpn. 1965, 38, 473-477.
15. (a) Miljanic, O. S.; Holmes, D.; Vollhardt, K. P. C. Org. Lett. 2005, 7, 4001-4004.
16. (b) Miljanic, O. S.; Han, S.; Holmes, D.; Schaller, G. R.; Vollhardt, K. P. C. Chem. Commun. 2005, 2606-2608.
17. (a) Toyota, S.; Yamamori, T.; Makino, T. Tetrahedron 2001, 57, 3521-3528.
18. (b) Toyota, S.; Makino, T. Tetrahedron Lett. 2003, 44, 7775-7778.
19. Bedard, T. C.; Moore. J. S. J. Am. Chem. Soc. 1995, 117, 10662-10671.
20. Nandy, R.; Subramoni, M.; Varghese, B.; Sankararaman, S. J. Org. Chem. 2007, 72, 938-944.
21. After repeated attempts, crystals of 1b of reasonable size for the structure determination could be obtained. The examination of the crystals with the polarizing microscope showed the crystals to have a poor degree of crystallinity (poor extinction). The quality of the reflections for higher angles was very poor, and there were only 1388 reflections with I > 2σ(I) out of 3678 unique reflections. There are 301 least squares parameters and 199 restraints in the refinement. An R factor of 0.117 for reflections I > 2σ(I) is reasonable for such data.
22. (a) Desiraju, G. R. Crystal Engineering. The Design of Organic Solids; Elsevier: Amsterdam, 1989; pp 92-96.
23. (b) For the crystal structure of pyrene, see: Robinson, J. M.; White, J. G. J. Chem. Soc. 1947, 358-368.
24. 1H NMR spectra of 1 and 2.
25. For comparison with [2,2]-2,7-pyrenophane, see: Umemoto, T.; Satani, S.; Sakata, Y.; Misumi, S. Tetrahedron Lett. 1975, 3159-3162.
26. (a) Venkataramana, G.; Sankararaman, S. Eur. J. Org. Chem. 2005, 4162-4166.
27. (b) Yang, S.-W.; Elangovan, A.; Hwang, K.-C.; Ho, T.-I. J. Phys. Chem. B 2005, 109, 16628-16635.
28. (a) Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 2nd ed.; Kulwer Academic: New York, 1999; pp 9 and 611.
29. (b) Berlman, I. B. Handbook of Fluorescence Spectra of Aromatic Molecules; Academic Press: New York, 1965; p 173.
30. Hamal, S.; Hirayama, F. J. Phys. Chem. 1983, 87, 83-89.
31. (a) Venkataramana, G.; Sankararaman, S. Org. Lett. 2006, 8, 2739-2742.
32. (b) Fechtenkötter, A.; Saalwächter, K.; Harbison, M. A.; Müllen, K.; Spiess, H. W. Angew. Chem., Int. Ed. 1999, 38, 3039-3042.
33. (c) Hynninen, P. H.; Lötjönen, S. Biochem. Biophys. Acta 1993, 1083, 374-380.
34. The δ value of H-10 in 2 was taken as that of pure 1a due to absence of π-stacking in 2, and the δ value of H-10 at 263 K (Figure 5) was taken as approximately equal to that of pure 1b to calculate the molar ratios 1a and 1b. Therefore, the equilibrium constant is only an approximate estimate.