Calix[4]pyrroles with bulky substituents and their anion binding studies

Calix[4]pyrroles with bulky substituents and their anion binding studies

Calix[4]pyrrole derivatives with bulky substituents at their meso-positions were synthesized via mixed condensation of pyrrole with cyclohexanone and acetophenone derivatives. Anion binding studies, carried out by isothermal titration calorimetry in 1,2-dichloroethane with Cl − and CH3 CO − 2 anions in the form of their tetrabutylammonium salts, revealed that these new calix[4]pyrrole derivatives can bind the aforementioned anions as effectively as the unsubstitutedparent system, octamethylcalix[4]pyrrole (1). Structural characterizations of new calix[4]pyrroles were carried out by using 1 H and 13 C NMR spectroscopy corroborated with mass spectrometry.

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  • 1. Beer, P. D.; Gale, P. A. Angew. Chem. Int. Ed. 2001, 40, 486-516.
  • 2. Sfriso, A.; Pavoni, B. Environ. Technol. 1994, 15, 1-14.
  • 3. Christianson, D. W.; Lipscomb, W. N. Acc. Chem. Res. 1989, 22, 62-69.
  • 4. Kavallieratos, K.; Bertao, C. M.; Crabtree, R. H. J. Org. Chem. 1999, 64, 1675-1683.
  • 5. Schanstra, J. P.; Janssen, D. B. Biochemistry 1996, 35, 5624-5632.
  • 6. V´ar´o, G.; Brown, L. S.; Needleman, R.; Lanyi, J. K. Biochemistry 1996, 35, 6604-6611.
  • 7. Glidewell, C. Chem. Br. 1990, 26, 137-140.
  • 8. Moss, B. Chem. Ind.-London 1996, 11, 407-411.
  • 9. Moyer, B. A.; Bonnesen, P. In Supramolecular Chemistry of Anions; Bianchi, A.; Bowman-James, K.; Garc´ıaEspa˜na, E., Eds. Wiley-VCH: New York, NY, USA, 1997.
  • 10. Dalil, H.; Biesemans, M.; Willem, R.; Angiolini, L.; Salatelli, E.; Caretti, D.; Chaniotakis, N. A.; Perdikaki, K. Helv. Chim. Acta 2002, 85, 852-866.
  • 11. Han, F.; Zhao, J. Helv. Chim. Acta 2008, 91, 635-645.
  • 12. Morf, W. E.; Huser, M.; Lindemann, B.; Schulthess, P.; Simon, W. Helv. Chim. Acta 1986, 69, 1333-1342.
  • 13. Ozay, H.; Yıldırım, M.; ¨ Ozay, ¨ O. ¨ Turk. J. Chem. 2015, 39, 777-788.
  • 14. Ren, H. X.; Zhao, M. G.; Wang, Y. J. Turk. J. Chem. 2010, 34, 731-737.
  • 15. Gale, P. A.; Sessler, J. L.; Kral, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140-5141.
  • 16. Sessler, J. L.; Anzenbacher, P.; Miyaji, H.; Jurs´ıkov´a, K.; Bleasdale, E. R.; Gale, P. A. Ind. Eng. Chem. Res. 2000, 39, 3471-3478.
  • 17. Akar, A.; Aydogan, A. J. Heterocycl. Chem. 2005, 42, 931-934.
  • 18. 18. Saha, I.; Park, K. H.; Han, M.; Kim, S. K.; Lynch, V. M.; Sessler, J. L.; Lee, C. H. Org. Lett. 2014, 16, 5414-5417.
  • 19. Baeyer, A. Berichte der deutschen chemischen Gesellschaft 1886, 19, 2184-2185 (in German).
  • 20. Bucher, C.; Zimmerman, R. S.; Lynch, V.; Kral, V.; Sessler, J. L. J. Am. Chem. Soc. 2001, 123, 2099-2100.
  • 21. Anzenbacher, P.; Nishiyabu, R.; Palacios, M. A. Coord. Chem. Rev. 2006, 250, 2929-2938.
  • 22. Dehaen, W.; Gale, P. A.; Garcia-Garrido, S. E.; Kostermans, M.; Light, M. E. New J. Chem. 2007, 31, 691-696.
  • 23. Anzenbacher, P.; Jursikova, K.; Shriver, J. A.; Miyaji, H.; Lynch, V. M.; Sessler, J. L.; Gale, P. A. J. Org. Chem. 2000, 65, 7641-7645.
  • 24. Nishiyabu, R.; Anzenbacher, P. J. Am. Chem. Soc. 2005, 127, 8270-8271.
  • 25. Miyaji, H.; Anzenbacher, P.; Sessler, J. L.; Bleasdale, E. R.; Gale, P. A. Chem. Commun. 1999, 1723-1724.
  • 26. Kaur, S.; Hwang, H.; Lee, J. T.; Lee, C. H. Tetrahedron Lett. 2013, 54, 3744-3747.
  • 27. Ghorpade, T. K.; Patri, M.; Mishra, S. P. Sensor. Actuat. B-Chem. 2016, 225, 428-435.
  • 28. Aydogan, A.; Lee, G.; Lee, C. H.; Sessler, J. L. Chem. Eur. J. 2015, 21, 2368-2376.
  • 29. Sokkalingam, P.; Hong, S. J.; Aydogan, A.; Sessler, J. L.; Lee, C. H. Chem. Eur. J. 2013, 19, 5860-5867.
  • 30. Aydogan, A.; Akar, A. Tetrahedron Lett. 2011, 52, 2790-2793.
  • 31. Aydogan, A.; Koca, A.; S¸ener, M. K.; Sessler, J. L. Org. Lett. 2014, 16, 3764-3767.
  • 32. Park, J. S.; Karnas, E.; Ohkubo, K.; Chen, P.; Kadish, K. M.; Fukuzumi, S.; Bielawski, C. W.; Hudnall, T. W.; Lynch, V. M.; Sessler, J. L. Science 2010, 329, 1324-1327.
  • 33. Custelcean, R.; Delmau, L. H.; Moyer, B. A.; Sessler, J. L.; Cho, W. S.; Gross, D.; Bates, G. W.; Brooks, S. J.; Light, M. E.; Gale, P. A. Angew. Chem., Int. Ed. 2005, 44, 2537-2542.
  • 34. Aydogan, A.; Akar, A. Chem. Eur. J. 2012, 18, 1999-2005.
  • 35. Aydogan, A.; Coady, D. J.; Lynch, V. M.; Akar, A.; Marquez, M.; Bielawski, C. W.; Sessler, J. L. Chem. Commun. 2008, 1455-1457.
  • 36. 36. Aydogan, A.; Coady, D. J.; Kim, S. K.; Akar, A.; Bielawski, C. W.; Marquez, M.; Sessler, J. L. Angew. Chem., Int. Ed. 2008, 47, 9648-9652.
  • 37. Silver, E. S.; Rambo, B. M.; Bielawski, C. W.; Sessler, J. L. J. Am. Chem. Soc. 2014, 136, 2252-2255.
  • 38. Aydogan, A. Supramol. Chem. 2016, 28, 117-124.
  • 39. Aydogan, A.; Sessler, J. L.; Akar, A.; Lynch, V. Supramol. Chem. 2008, 20, 11-21.
  • 40. Levitskaia, T. G.; Marquez, M.; Sessler, J. L.; Shriver, J. A.; Vercouter, T.; Moyer, B. A. Chem. Commun. 2003,
  • 2248-2249. 41. Aydogan, A.; Akar, A. Helv. Chim. Acta 2014, 97, 1427-1432.
  • 42. Anzenbacher, P.; Jursikova, K.; Lynch, V. M.; Gale, P. A.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 11020-11021.
  • 43. Gil-Ram´ırez, G.; Escudero-Ad´an, E. C.; Benet-Buchholz, J.; Ballester, P. Angew. Chem. Int. Ed. 2008, 47, 4114- 4118.