Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Charge-Transfer Complex Formation between Stilbenes and 7,7,8,8-Tetracyanoquinodimethane

  • Jin, Jung-Il (Chemistry Department, College of Sciences, Korea University) ;
  • Kim, Joon-Seop (Chemistry Department, College of Sciences, Korea University) ;
  • Kim, Jeong-Deuk (Chemistry Department, College of Sciences, Korea University)
  • Published : 1988.06.20
Download PDF
⟨ Previous Next ⟩

Abstract

Formation of intermolecular charge-transfer complexes between 7,7,8,8-tetracyanoquinodimethane (TCNQ) and two different series of stilbene derivatives has been studied spectroscopically at $25^{\circ}$C in 1,2-dichloroethane. The compounds of Series I include stilbene and derivatives which have fused phenyl rings on one end of the central ethylene structure and a phenyl ring on the other end. The other Series, II, is comprised of stilbenes which have various para substituents on one of the two phenyl rings. The equilibrium constant, $K_c^{AD}$ and the molar extinction coefficient, ${\varepsilon}_{\lambda}^{AD}$, were determined using the Scott equation. The values of the charge-transfer transition frequency, ${\vu}_AD$ and $K_c{AD}$ correlated well respectively with the ionization potentials of the fused rings of Series Ⅰ or of the compounds of Series II and with the values of ${\sigma}_p$, the Hammett constants of the Series II substituents. trans-4-N,N-Dimethylaminostilbene and trans-4-nitrostilbene were found to be able to participate in electron transfer reaction with TCNQ forming the corresponding anion radical, TCNQ$^-$:

Keywords

References

  1. J. Am. Chem. Soc. v.72 R. S. Mulliken
  2. J. Am. Chem. Soc. v.74 R. S. Mulliken
  3. J. Am. Chem. Soc. v.71 H. A. Benesi;J.H. Hildebrand
  4. Proc. Int. Conf. on Coordination Compounds R. L. Scott
  5. J. Am. Chem. Soc. v.84 L. R. Melby;R. J. Harder;W. R. Hertler;W. Mahler;R. E. Benson;W. E. Mochel
  6. Trans. Faraday Soc. v.62 A. R. Cooper;C. W. P. Crowne;P. G. Farrell
  7. Organic Charge-Transfer Complexes R. Foster
  8. J. Chem. Soc., Perkin Trans. 1 v.2 K. Yamasaki;T. Yonezawa
  9. J. Am. Chem. Soc. v.98 R. C. Wheland;J. L. Gillson
  10. J. Chem. Phys. v.45 R. S. Becker;E. Chen
  11. J. Chem. Soc., Chem. Commun. F. Wudle;G. M. Smith;E. J. Hufnager
  12. J. Am. Chem. Soc. v.103 K. Bechgaad;K. Carneiro;F. B. Rasmussen;M. Olsen
  13. J. Prakt. Chem. v.319 V. J. Jamrozik
  14. J. Am. Chem. Soc. v.95 J. Ferraris;D. V. Cowan;V. V. Walatkax, Jr.;J. H. Perstein
  15. J. Chem. Soc. J. Weiss
  16. Tetrahedron Suppl. v.7 M. J. S. Dewar;C. C. Thompson, Jr.
  17. Physical Organic Chemistry L. P. Hammett
  18. J. Org. Chem. v.23 D. H. McDaniel;H. C. Brown
  19. Nippon Kagaku Kaishi v.1 T. Tomono;E. Hasegawa;E. Tsuchida
  20. Organic Charge-Transfer Complexes R. Foster
  21. J. Org. Chem. v.37 M. F. Ruasse;J. E. Dubois
  22. J. Am. Chem Soc. v.77 H. O. House
  23. Tetrahedron Lett. v.19 N. Ono;S. Kawai;K. Tanaka;A. Kaji
  24. J. Org. Chem. v.48 H. D. Becker;K. Anderson
  25. J. Chem. Soc. J. L. Everett;G. A. R. Kon
  26. Bull. Chem. Soc. Jpn. v.51 M. Matsumoto;S. Dobashi;K. Kondo
  27. Laboratory Experiments in Organic Chemistry R. Adams;J. R. Johnson;C. E. Wilcox, Jr.
  28. Laboratory Experiments in Organic Chemistry R. Adams;J. R. Johnson;C. E. Wilcox, Jr.

Cited by

  1. ChemInform Abstract: Charge‐Transfer Complex Formation Between Stilbenes and 7,7,8,8‐Tetracyanoquinodimethane. vol.20, pp.1, 1988, https://doi.org/10.1002/chin.198901134
  2. Experimental investigations by using electrochemical, steady state and time resolved spectroscopic tools on the photoreactions of disubstituted indoles in presence of tetracyanoquinodimethane (TCNQ) a vol.188, pp.2, 1988, https://doi.org/10.1016/j.jphotochem.2006.12.018