3,5,7,9‐Tetraphenylhexaazaacridine: A Highly Stable, Weakly Antiaromatic Species with 16 π Electrons
2005; Wiley; Volume: 44; Issue: 33 Linguagem: Inglês
10.1002/anie.200500831
ISSN1521-3773
AutoresPeter Langer, Anja Bodtke, N. S. Saleh, Helmar Görls, Peter R. Schreiner,
Tópico(s)Photochemistry and Electron Transfer Studies
ResumoAngewandte Chemie International EditionVolume 44, Issue 33 p. 5255-5259 Communication 3,5,7,9-Tetraphenylhexaazaacridine: A Highly Stable, Weakly Antiaromatic Species with 16 π Electrons† Peter Langer Prof. Dr., Peter Langer Prof. Dr. [email protected] Institut für Chemie, Universität Rostock, Albert-Einstein-Strasse 3a, 18059 Rostock, Germany, Fax: (+49) 381-498-6412 Leibniz-Institut für Organische Katalyse (IfOK) an der Universität Rostock e.V. Albert-Einstein-Strasse 29a, 18059 Rostock, GermanySearch for more papers by this authorAnja Bodtke Dr., Anja Bodtke Dr. Institut für Chemie und Biochemie, Ernst-Moritz-Arndt Universität Greifswald, Soldmannstrasse 16, 17487 Greifswald, GermanySearch for more papers by this authorNehad N. R. Saleh Dr., Nehad N. R. Saleh Dr. Institut für Chemie und Biochemie, Ernst-Moritz-Arndt Universität Greifswald, Soldmannstrasse 16, 17487 Greifswald, GermanySearch for more papers by this authorHelmar Görls Dr., Helmar Görls Dr. Institut für Anorganische und Analytische Chemie, Universität Jena, August-Bebel-Strasse 2, 07740 Jena, GermanySearch for more papers by this authorPeter R. Schreiner Prof. Dr., Peter R. Schreiner Prof. Dr. [email protected] Institut für Organische Chemie, Justus-Liebig-Universität, Heinrich-Buff-Ring 58, 35392 Giessen, Germany, Fax: (+49) 641-99-34309 The University of Georgia, Department of Chemistry, Athens, GA, USASearch for more papers by this author Peter Langer Prof. Dr., Peter Langer Prof. Dr. [email protected] Institut für Chemie, Universität Rostock, Albert-Einstein-Strasse 3a, 18059 Rostock, Germany, Fax: (+49) 381-498-6412 Leibniz-Institut für Organische Katalyse (IfOK) an der Universität Rostock e.V. Albert-Einstein-Strasse 29a, 18059 Rostock, GermanySearch for more papers by this authorAnja Bodtke Dr., Anja Bodtke Dr. Institut für Chemie und Biochemie, Ernst-Moritz-Arndt Universität Greifswald, Soldmannstrasse 16, 17487 Greifswald, GermanySearch for more papers by this authorNehad N. R. Saleh Dr., Nehad N. R. Saleh Dr. Institut für Chemie und Biochemie, Ernst-Moritz-Arndt Universität Greifswald, Soldmannstrasse 16, 17487 Greifswald, GermanySearch for more papers by this authorHelmar Görls Dr., Helmar Görls Dr. Institut für Anorganische und Analytische Chemie, Universität Jena, August-Bebel-Strasse 2, 07740 Jena, GermanySearch for more papers by this authorPeter R. Schreiner Prof. Dr., Peter R. Schreiner Prof. Dr. [email protected] Institut für Organische Chemie, Justus-Liebig-Universität, Heinrich-Buff-Ring 58, 35392 Giessen, Germany, Fax: (+49) 641-99-34309 The University of Georgia, Department of Chemistry, Athens, GA, USASearch for more papers by this author First published: 15 August 2005 https://doi.org/10.1002/anie.200500831Citations: 27 † This work was supported by the German state of Mecklenburg-Western Pomerania (scholarship for A.B.), the Dr. Dr. Gerda-von-Mach Gedächtnisstiftung (scholarship for N.N.R.S.), and the Deutsche Forschungsgemeinschaft. P.R.S. was supported at UGA through the National Science Foundation (CHE-0209827). Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Graphical Abstract Zwitterionic structures with very low lying triplet states are the dominant characteristics of the first hexaazaacridine, 3,5,7,9-tetraphenylhexaazaacridine (TPH-acridine, see picture), and the analogous TPH-anthracene. The structure and spectroscopic properties were studied experimentally and by DFT calculations and analysis of nucleus-independent chemical shifts. References 1For oligothiophenes with low-lying triplet states see: 1aF. Garnier, Angew. Chem. 1989, 101, 529; Angew. Chem. Int. Ed. Engl. 1989, 28, 513; 1bF. Garnier, A. Yassar, R. Hajlaoui, G. Horowitz, F. Deloffre, B. Servet, S. Ries, P. Alnot, J. Am. Chem. Soc. 1993, 115, 8716; 1cF. Garnier, R. Hajlaoui, A. Yassar, P. Srivastava, Science 1994, 265, 1684; 1dA. Dodabalapur, L. Torsi, H. E. Katz, Science 1995, 268, 270; 1eA. Dodabalapur, L. J. Rothberg, A. W. P. Fung, H. E. Katz, Science 1996, 272, 1462; a low-lying triplet state was predicted for the not-yet-synthesized cyclohepta[def]fluorene: 1fU. Grieser, K. Hafner, Chem. Ber. 1994, 127, 2307, and references therein. 2P. Pierron, Ann. Chim. Phys. 1908, 15, 269. 3K. A. Hutchison, G. Srdanov, R. Hicks, H. Yu, F. Wudl, T. Strassner, M. Nendel, K. N. Houk, J. Am. Chem. Soc. 1998, 120, 2989. 4K. A. Hutchison, K. Hasharoni, F. Wudl, A. Berg, Z. Shuali, H. Levanon, J. Am. Chem. Soc. 1998, 120, 6362. 5 5aP. v. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. van Eikema Hommes, J. Am. Chem. Soc. 1996, 118, 6317. 6 6aA. D. Becke, J. Chem. Phys. 1993, 98, 5648; 6bC. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785. 7R. Singh, B. M. Deb, Phys. Rep. 1999, 311, 48. 8T. Clark, J. Chandrasekhar, Isr. J. Chem. 1993, 33, 435. 9P. v. R. Schleyer, M. Manoharan, Z.-X. Wang, B. Kiran, H. Jiao, R. Puchta, N. J. R. van Eikema Hommes, Org. Lett. 2001, 3, 2465. 10V. Gogonea, P. v. R. Schleyer, P. R. Schreiner, Angew. Chem. 1998, 110, 2045; Angew. Chem. Int. Ed. 1998, 37, 1945. 11Whereas a variety of cationic cyanine dyes are known, stable anionic cyanines are rare. TPH-acridine (2) represents, with the exception of 1, the first molecule with a nitrogen-based anionic cyanine moiety: 11aP. F. Gordon, P. Gregory, Organic Chemistry in Colour, Springer, Berlin, 1983; 11bD. R. Waring, G. Hallas, The Chemistry and Application of Dyes (Eds.: ), Plenum, New York, 1990. Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z500831_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume44, Issue33August 19, 2005Pages 5255-5259 ReferencesRelatedInformation
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