Conformational analysis of 3,3′-, 3,4′- and 4,4′-dimethoxy-2,2′-bithiophenes as models for related polymers

(Note: The full text of this document is currently only available in the PDF Version )

Alessandro Bongini, Federica Brioni and Mauro Panunzio


Abstract

An analysis of 13C chemical shifts of quaternary carbons of 3,3′-, 3,4′- and 4,4′-dimethoxy-2,2′-bithiophenes indicates they can be a useful tool for the identification of the inter-ring junction type. UV spectra and theoretical calculations are used to perform a conformational analysis of the compounds. The results show that the compounds prefer a non-planar conformation in non-condensated phases. The reasons for this non-planarity of the dimers and the effect on related polymers are discussed.


References

  1. (a) A. Chang, R. L. Blankespoor and L. L. Miller, J. Electroanal. Chem., 1987, 236, 239 CrossRef CAS; (b) A. Chang and L. L. Miller, Synth. Met., 1987, 22, 71 CrossRef CAS; (c) S. Tanaka, M. Sato and K. Kaeriyama, Synth. Met., 1988, 25, 277 CrossRef CAS; (d) K. Kaeriyama, S. Tanaka, M. Sato and K. Hamada, Synth. Met., 1989, 28, C611 CAS; (e) T. Yamamoto, A. Kashiwazaki and K. Kato, Makromol. Chem., 1989, 190, 1649 CrossRef CAS; (f) M. Feldhues, G. Kämpf, H. Litterer, T. Mecklenburg and P. Wegener, Synth. Met., 1989, 28, C487 CAS; (g) L. H. Shi, F. Garnier and J. Roncali, Synth. Met., 1991, 41–43, 547; (h) M. Dietrich and J. Heinze, Synth. Met., 1991, 41–43, 503 CrossRef CAS; (i) J. Daoust and M. Leclerc, Macromol., 1991, 24, 455 Search PubMed; (j) J. Roncali, Chem. Rev., 1992, 92, 711 CrossRef CAS; (k) P. Tschuncky and J. Heinze, Synth. Met., 1993, 55–57, 1603 CrossRef; (l) G. Zotti, M. C. Gallazzi, G. Zerbi and S. V. Meille, Synth. Met., 1995, 73, 217 CrossRef CAS.
  2. (a) J. L. Bredas, G. B. Street, B. Themans and J. M. André, J. Chem. Phys., 1985, 83, 1323 CrossRef CAS; (b) M. Leclerc and R. E. Proud'homme, Polym. Bull., 1987, 18, 159 CAS; (c) R. M. Souto Maior, K. Hinkelmann, H. Eckert and F. Wudl, Macromol., 1990, 23, 1268 Search PubMed.
  3. (a) G. Barbarella, A. Bongini and M. Zambianchi, Macromol., 1994, 27, 3039 Search PubMed; (b) G. Barbarella, M. Zambianchi, L. Antolini, U. Folli, F. Goldoni, D. Iarossi, L. Schenetti and A. Bongini, J. Chem. Soc., Perkin. Trans. 2, 1995, 1869 RSC.
  4. (a) H. Satonaka, Bull. Chem. Soc. Jpn., 1983, 56, 2463 CAS; (b) K. Takahashi, T. Sone and K. Fujiada, J. Phys. Chem., 1970, 74, 2765 CrossRef CAS.
  5. S. V. Meille, A. Farina, F. Bezziccheri and M. C. Gallazzi, Adv. Mater., 1994, 6, 848 CrossRef CAS.
  6. (a) G. Barbarella, A. Bongini and M. Zambianchi, Adv. Mater., 1991, 3, 494 CrossRef CAS; (b) C. Arbizzani, G. Barbarella, A. Bongini, M. Mastragostino and M. Zambianchi, Synth. Met., 1992, 52, 329 CrossRef CAS.
  7. (a) E. F. Paulus, R. Dammel, G. Kämpf, P. Wegener, K. Siam, K. Wolinski and L. Schäfer, Acta Crystallogr., Sect. B, 1988, 44, 509 CrossRef; (b) E. F. Paulus, K. Siam, K. Wolinski and L. Schäfer, J. Mol. Struct., 1989, 196, 171 CrossRef CAS.
  8. S. Samdal, E. J. Samuelsen and H. V. Volden, Synth. Met., 1993, 59, 259 CrossRef CAS.
  9. (a) G. Barbarella, M. Zambianchi, G. Bongini and L. Antolini, Adv. Mater., 1992, 4, 282 CrossRef CAS; (b) 1993, 5, 834.
  10. N. L. Allinger and Y. H. Yuh, MM2(91), Quantum Chemistry Program Exchange, Indiana University, Bloomington, IN 47405, USA.
  11. M. Rajzmann and P. François, QCMP029, Quantum Chemistry Program Exchange, Indiana University, Bloomington, IN 47405, USA.
  12. J. J. P. Stewart, MOPAC 6.0, Quantum Chemistry Program Exchange, Indiana University, Bloomington, IN 47405, USA.
  13. L. L. Miller and Y. Yu, J. Org. Chem., 1995, 60, 6813 CrossRef CAS.
  14. P. Wegener and M. Feldhuis, Chem. Abstr., 1992, 117, 233842a Search PubMed.
  15. (a) J. K. Stille, Angew. Chem., Int. Ed. Engl., 1986, 25, 508 CrossRef; (b) V. Farina and C. Krishnan, J. Am. Chem. Soc., 1991, 113, 9585 CrossRef CAS; (c) Z. Bao, W. K. Chan and Y. Yu, J. Am. Chem. Soc., 1995, 117, 12 426 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.