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Synthesis of Stilbene Crown Ether Calix[4]arene and their isomerization

Synthesis of Stilbene Crown Ether Calix[4]arene and their isomerization. Synthesis of Stilbene Crown Ether Calix[4]arene and their isomerization. Synthesis of Stilbene Crown Ether Calix[4]arene and their isomerization. Synthesis of Stilbene Crown Ether Calix[4]arene and their isomerization.

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Synthesis of Stilbene Crown Ether Calix[4]arene and their isomerization

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  1. Synthesis of Stilbene Crown Ether Calix[4]arene and their isomerization Synthesis of Stilbene Crown Ether Calix[4]arene and their isomerization Synthesis of Stilbene Crown Ether Calix[4]arene and their isomerization Synthesis of Stilbene Crown Ether Calix[4]arene and their isomerization Synthesis of Stilbene Crown Ether Calix[4]arene and their isomerization Synthesis of Stilbene Crown Ether Calix[4]arene and their isomerization Synthesis of Stilbene Crown Ether Calix[4]arene and their isomerization Synthesis of Stilbene Crown Ether Calix[4]arene and their isomerization Synthesis of Stilbene Crown Ether Calix[4]arene and their isomerization Synthesis of Stilbene Crown Ether Calix[4]arene and their isomerization • By Synthesis of Stilbene Crown Ether Calix[4]arene and their isomerization Mr. Rojrit Rojanathanes Assist.Prof.Dr. Tawatchai Tuntulani Assist.Prof.Dr. Mongkol Sukwattanasinitt* http://www.student.chula.ac.th/~b3819023

  2. Overview Introduction Objective Results

  3. Marsella, M.J.; Carroll, P.J.; Swager, T.M. J.Am.Chem.Soc.1994, 116, 9347. • Marsella, M.J.; Carroll, P.J.; Swager, T.M. J.Am.Chem.Soc.1995, 117, 9832. • Marsella, M.J.; Swager, T.M. J.Am.Chem.Soc.1993, 115, 12214. Introduction Receptor Guest • Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev.1995, 197. Ion Receptor Molecular Receptor

  4. Bohmer, V. Angew. Chem. Int. Ed. Engl.1995, 34, 713. • Gutsche, C. D.; Iqbal, M. Org. Syn.1990, 68, 234. • Saadioui, M.; Asfari, Z.; Vicens, J. Tetrahedron Lett.1997, 38, 1187. Calixarenes Doing further functionalization easily Calix[4]arene, the molecular platform

  5. Azobenzene Crown Calix • Pipoosananakaton, B.; Sukwattanasinitt, M.; Jaiboon, N.; Chaichit, N.; Tuntulani, T. • Bull. Kor. Chem. Soc.2000, 21, 867. • Pipoosananakaton, B.; Sukwattanasinitt, M.; Jaiboon, N.; Chaichit, N.; Tuntulani, T. • Tetrahedron Lett.2000, 41, 9095.

  6. Isomerization Twisting about the N=N Inversion at one of the N atomscauses thermal isomerization

  7. Stilbene lmaxemaxlmaxemax 222 25,000 229 15,800 283 12,300 295 25,000 308 25,000 320 15,800

  8. M1+ M1+ hn M2+ Stilbene Crown Calix Calix[4]arene, the molecular platform Dialdehyde Calix[4]arene, the key intermediate

  9. Objective Synthesize stilbene crown ether calix[4]arenes Study the photo-isomerization properties of the synthesized calix[4]arenes

  10. K2CO3, CH3CN, Bu4N+Br- Synthesis Strategy • Navakun K.; Tuntulani T.; Ruangpornvisuti V. • J. Inclu. Phenom.2000, 38, 113.

  11. TiCl4 Zn, THF McMurry Coupling • Lenoir, D. Synthesis1989, 883. • Ephritikhine, M. Chem Commun.1998, 2549.

  12. Calixarene Derivatization • Sukwattanasinitt M.; Rojanathanes, R.; Tuntulani T.; Sritana-Anant, Y.; • Ruangpornvisuti V.Tetrahedron Lett.2001, 42, 5291.

  13. NMR Characterization * * • Sukwattanasinitt M.; Rojanathanes, R.; Tuntulani T.; Sritana-Anant, Y.; • Ruangpornvisuti V.Tetrahedron Lett.2001, 42, 5291.

  14. UV-Vis Characterization • Sukwattanasinitt M.; Rojanathanes, R.; Tuntulani T.; Sritana-Anant, Y.; • Ruangpornvisuti V.Tetrahedron Lett.2001, 42, 5291.

  15. Monoclinic P21/c R = 0.0931 a = 20.7486(5) A b = 12.3713(4) A c = 22.6335(5) A b = 109.373(2)o o o o X-Ray Confirmation

  16. Transition State

  17. Photo-isomerization Using Hg lamp Isomerization properties

  18. Photo-Stationary State

  19. Further Derivatization

  20. Tetra-substituted calix

  21. Photo-Stationary State

  22. Acknowledgement National Science and Technology Development Agency The Thailand Research Fund Ministry of University Affairs Scientific and Technological Research Equipment Centre

  23. Thank you for your attention Available on the web www.student.chula.ac.th/~b3819023

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