Synthesis of the porphyrin-fused porphyrin, [2]porphyracene

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

Ken-ichi Sugiura, Takuya Matsumoto, Satoshi Ohkouchi, Yasuhisa Naitoh, Tomoji Kawai, Yoshio Takai, Kantaro Ushiroda and Yoshiteru Sakata


Abstract

A novel porphyrin-fused porphyrin is formed by an oligomerization reaction of a (porphyrinato)nickel complex with TeCl4; the isolated compound, [2]porphyracene, was characterized by spectroscopic methods and direct observation using scanning tunnelling microscopy; the excitation energy value of 13460 cm–1 (743 nm) is the lowest value reported for porphyrin dimers.


References

  1. Porphyrins and Metalloporphyrin, ed. K. M. Smith, Elsevier, Amsterdam, 1975 Search PubMed; The Porphyrins, ed. D. Dolphin, Academic Press, New York, 1978, vol. 8 Search PubMed.
  2. V. S.-Y. Lin, S. G. DiMagno and M. J. Therien, Science, 1994, 264, 1105 CrossRef CAS; V. S.-Y. Lin and M. J. Therien, Chem. Eur. J., 1995, 1, 645 CrossRef CAS.
  3. J. L. Sessler and S. J. Weghorn, Expanded, Contracted & Isomeric Porphyrins, ed. J. E. Baldwin, F. R. S. Magnus and P. D. Magnus, Pergamon, New York, 1997 Search PubMed.
  4. M. J. Crossley and P. L. Burn, J. Chem. Soc., Chem. Commun., 1987, 39 RSC.
  5. L. Jaquinod, O. Siri, R. G. Khoury and K. M. Smith, Chem. Commun., 1998, 1261 RSC.
  6. (a) K. Susumu, T. Shimidzu, K. Tanaka and H. Segawa, Tetrahedron Lett., 1996, 37, 8399 CrossRef CAS; (b) A. Osuka and H. Shimizu, Angew. Chem., Int. Ed. Engl., 1997, 36, 135 CrossRef CAS; (c) R. G. Khoury, L. Jaquinod and K. M. Smith, Chem. Commun., 1997, 1057 RSC; (d) T. Ogawa, Y. Nishimoto, N. Yoshida, N. Ono and A. Osuka, Chem. Commun., 1998, 337 RSC; (e) T. Ogawa, Y. Nishimoto, N. Yoshida, N. Ono and A. Osuka, Angew. Chem., Int. Ed., 1999, 38, 176 CrossRef CAS.
  7. T. D. Lash, S. T. Chaney and D. T. Richter, J. Org. Chem., 1998, 63, 9076 CrossRef CAS.
  8. K.-i. Sugiura, M. R. Kumar, T. K. Chandrashekar and Y. Sakata, Chem. Lett., 1997, 291 CrossRef CAS; K.-i. Sugiura, K. Ushiroda, T. Tanaka, M. Sawada and Y. Sakata, Chem. Lett., 1997, 927 CAS.
  9. The reductive aryl coupling reaction of bis(aryl)tellurium dichloride is well established: J. Bergman, Tetrahedron, 1972, 28, 3323 Search PubMed; J. Bergman, R. Carlsson and B. Sjöberg, in Organic Synthesis, ed. W. E. Noland, Wiley, New York, 1988, coll. vol. VI, pp. 468–471 CrossRef CAS.
  10. T. Takami, J. K. Gimzewski, R. R. Schlittler, T. Jung, Ch. Gerber, K. Sugiura and Y. Sakata, Abstracts of Papers, 50th National Meeting of the Japanese Physical Society, Kanagawa, Japanese Physical Society, Tokyo, 1995, Abstract 28p-PSB-29 Search PubMed; T. A. Jung, R. R. Schlittler, J. K. Gimzewski, H. Tang and C. Joachim, Science, 1996, 271, 181 Search PubMed; T. A. Jung, R. R. Schlittler and J. K. Gimzewski, Nature, 1997, 386, 696 CrossRef CAS; J. K. Gimzewski and C. Joachim, Science, 1999, 283, 1683 CAS.
  11. In the iodination reaction of 5,15-diphenylporphyrin, the second substitution reaction occurs at the β-position: R. W. Boyle, C. K. Johnson and D. Dolphin, J. Chem. Soc., Chem. Commun., 1995, 527 Search PubMed; A. Nakano, H. Shimidzu and A. Osuka, Tetrahedron Lett., 1998, 39, 9489 RSC.
Click here to see how this site uses Cookies. View our privacy policy here.