No Access

meso-aryl expanded porphyrins: synthesis, structures, and coordination chemistry

Department of Chemistry, Graduate School of Science, Kyoto University, Core Research for Evolutional Science and Technology (CREST), Japan Science and Technology Agency (JST), Kyoto 606-8502, Japan

Search for more papers by this author

and

Atsuhiro Osuka

Department of Chemistry, Graduate School of Science, Kyoto University, Core Research for Evolutional Science and Technology (CREST), Japan Science and Technology Agency (JST), Kyoto 606-8502, Japan

Corresponding author, fax: +81 75-753-3970.

Search for more papers by this author

https://doi.org/10.1142/S1088424604000167Cited by:30 (Source: Crossref)

Abstract

meso-aryl expanded porphyrins, that can be regarded as real homologues of meso-tetraaryl porphyrins, were prepared by our synthetic protocol under the modified Rothemund-Lindsey conditions. This new class of molecules exhibits interesting spectral, electrochemical, and coordination properties. These promising features are emphasized, with a particular attention on the annulenic properties.

Dedicated to Professor Hisanobu Ogoshi on the occasion of his 70^th birthday

Keywords:

Most comprehensive & up-to-date research on PORPHYRINS
Handbook of Porphyrin Science now available in 46 volumes

References

R. B. Woodward , Aromaticity Conference ( Sheffield , 1966 ) . Google Scholar
V. J. Baueret al., J. Am. Chem. Soc. 105, 6429 (1983), DOI: 10.1021/ja00359a012. Crossref, Web of Science, Google Scholar
J. L. Sessleret al., J. Am. Chem. Soc. 112, 2810 (1990), DOI: 10.1021/ja00163a059. Crossref, Web of Science, Google Scholar
J. L. Sessler, A. Gebauer and S. J. Weghorn, The Porphyrin Handbook 2, eds. K. M. Kadish, K. M. Smith and R. Guilard (Academic Press, San Diego, 1999) pp. 55–124. Google Scholar
J. L. Sessler and D. Seidel, Angew. Chem. Int. Ed. 42, 5134 (2003), DOI: 10.1002/anie.200200561. Crossref, Web of Science, Google Scholar
A. Jasat and D. Dolphin, Chem. Rev. 97, 2267 (1997), DOI: 10.1021/cr950078b. Crossref, Web of Science, Google Scholar
T. D. Lash, Angew. Chem. Int. Ed. 39, 1763 (2000). Crossref, Web of Science, Google Scholar
H. Furuta, H. Maeda and A. Osuka, Chem. Commun. (Cambridge, U. K.) 1795 (2002), DOI: 10.1039/b200525p. Google Scholar
M. Shionoyaet al., J. Am. Chem. Soc. 114, 5714 (1992), DOI: 10.1021/ja00040a034. Crossref, Web of Science, Google Scholar
J. L. Sessler and J. M. Davis, Acc. Chem. Res. 34, 989 (2001), DOI: 10.1021/ar980117g. Crossref, Web of Science, Google Scholar
R. Bonnet, Chem. Soc. Rev. 24, 19 (1995), DOI: 10.1039/cs9952400019. Crossref, Web of Science, Google Scholar
J. L. Sessleret al., J. Am. Chem. Soc. 118, 12322 (1996), DOI: 10.1021/ja961672l. Crossref, Web of Science, Google Scholar
S. L. Springset al., J. Am. Chem. Soc. 121, 2281 (1999), DOI: 10.1021/ja9835436. Crossref, Web of Science, Google Scholar
P. Caravanet al., Chem. Rev. 99, 2293 (1999), DOI: 10.1021/cr980440x. Crossref, Web of Science, Google Scholar
J. Setsune and S. Maeda, J. Am. Chem. Soc. 122, 12405 (2000), DOI: 10.1021/ja005588o. Crossref, Web of Science, Google Scholar
J. Setsune, Y. Katakami and N. Iizuna, J. Am. Chem. Soc. 121, 8957 (1999), DOI: 10.1021/ja991669c. Crossref, Web of Science, Google Scholar
A. Krivokapac, A. R. Cowley and H. L. Anderson, J. Org. Chem. 68, 1089 (2003). Crossref, Web of Science, Google Scholar
T. K. Chandrashekar and S. Venkatraman, Acc. Chem. Res. 36, 676 (2003), DOI: 10.1021/ar020284n. Crossref, Web of Science, Google Scholar
D. Seidel, V. Lynch and J. L. Sessler, Angew. Chem. Int. Ed. 41, 1422 (2002). Crossref, Web of Science, Google Scholar
T. Köhleret al., J. Am. Chem. Soc. 125, 6872 (2003), DOI: 10.1021/ja035089y. Crossref, Web of Science, Google Scholar
J. Y. Shinet al., J. Am. Chem. Soc. 123, 7190 (2001), DOI: 10.1021/ja0106624. Crossref, Web of Science, Google Scholar
J. Y. Shin, H. Furuta and A. Osuka, Angew. Chem. Int. Ed. 40, 619 (2001). Crossref, Web of Science, Google Scholar
S. Shimizuet al., Angew. Chem. Int. Ed. 42, 78 (2003), DOI: 10.1002/anie.200390058. Crossref, Web of Science, Google Scholar
R. Taniguchiet al., Tetrahedron Lett. 44, 2505 (2003), DOI: 10.1016/S0040-4039(03)00328-9. Crossref, Web of Science, Google Scholar
M. G. P. M. S. Neveset al., Chem. Commun. (Cambridge, U. K.) 385 (1999), DOI: 10.1039/a808952c. Google Scholar
E. Vogelet al., Angew. Chem. Int. Ed. 34, 2511 (1995). Crossref, Web of Science, Google Scholar
M. Bröringet al., Angew. Chem. Int. Ed. 34, 2515 (1995). Crossref, Web of Science, Google Scholar
N. Sprutta and L. Latos-Grazynski, Chem.—-Eur. J. 23, 5099 (2001). Google Scholar
V. G. Anandet al., J. Am. Chem. Soc. 123, 8620 (2001), DOI: 10.1021/ja011265w. Crossref, Web of Science, Google Scholar
M. Suzuki and A. Osuka, Org. Lett. 5, 3943 (2003), DOI: 10.1021/ol035650x. Crossref, Web of Science, Google Scholar
C. Brückneret al., Chem Commun. (Cambridge, U. K.) 1689 (1997), DOI: 10.1039/a704510g. Google Scholar
Y. Tanaka et al. , Am. Chem. Soc. . Google Scholar