Azacalixphyrin: The Hidden Porphyrin Cousin Brought to Light†
Zhongrui Chen
CINaM, UMR 7325 CNRS, Aix-Marseille Université, Campus Luminy, case 913, 13288 Marseille Cedex 09 (France)
Search for more papers by this authorDr. Michel Giorgi
Spectropole, FR1739 CNRS, Aix-Marseille Université, Campus St Jérôme, case D11, 13397 Marseille Cedex 20 (France)
Search for more papers by this authorCorresponding Author
Prof. Denis Jacquemin
CEISAM UMR CNRS 6230, Université de Nantes, 2, rue de la Houssinière, BP 92208 4322 NANTES Cedex 3 (France)
Institut Universitaire de France, 103 blvd St Michel, 75005 Paris Cedex 05 (France)
Denis Jacquemin, CEISAM UMR CNRS 6230, Université de Nantes, 2, rue de la Houssinière, BP 92208 4322 NANTES Cedex 3 (France)
Olivier Siri, CINaM, UMR 7325 CNRS, Aix-Marseille Université, Campus Luminy, case 913, 13288 Marseille Cedex 09 (France)
Search for more papers by this authorDr. Mourad Elhabiri
Laboratoire de Chimie Moléculaire, UMR 7509 CNRS, Université de Strasbourg, 25, rue Becquerel, 67200 Strasbourg (France)
Search for more papers by this authorCorresponding Author
Dr. Olivier Siri
CINaM, UMR 7325 CNRS, Aix-Marseille Université, Campus Luminy, case 913, 13288 Marseille Cedex 09 (France)
Denis Jacquemin, CEISAM UMR CNRS 6230, Université de Nantes, 2, rue de la Houssinière, BP 92208 4322 NANTES Cedex 3 (France)
Olivier Siri, CINaM, UMR 7325 CNRS, Aix-Marseille Université, Campus Luminy, case 913, 13288 Marseille Cedex 09 (France)
Search for more papers by this authorZhongrui Chen
CINaM, UMR 7325 CNRS, Aix-Marseille Université, Campus Luminy, case 913, 13288 Marseille Cedex 09 (France)
Search for more papers by this authorDr. Michel Giorgi
Spectropole, FR1739 CNRS, Aix-Marseille Université, Campus St Jérôme, case D11, 13397 Marseille Cedex 20 (France)
Search for more papers by this authorCorresponding Author
Prof. Denis Jacquemin
CEISAM UMR CNRS 6230, Université de Nantes, 2, rue de la Houssinière, BP 92208 4322 NANTES Cedex 3 (France)
Institut Universitaire de France, 103 blvd St Michel, 75005 Paris Cedex 05 (France)
Denis Jacquemin, CEISAM UMR CNRS 6230, Université de Nantes, 2, rue de la Houssinière, BP 92208 4322 NANTES Cedex 3 (France)
Olivier Siri, CINaM, UMR 7325 CNRS, Aix-Marseille Université, Campus Luminy, case 913, 13288 Marseille Cedex 09 (France)
Search for more papers by this authorDr. Mourad Elhabiri
Laboratoire de Chimie Moléculaire, UMR 7509 CNRS, Université de Strasbourg, 25, rue Becquerel, 67200 Strasbourg (France)
Search for more papers by this authorCorresponding Author
Dr. Olivier Siri
CINaM, UMR 7325 CNRS, Aix-Marseille Université, Campus Luminy, case 913, 13288 Marseille Cedex 09 (France)
Denis Jacquemin, CEISAM UMR CNRS 6230, Université de Nantes, 2, rue de la Houssinière, BP 92208 4322 NANTES Cedex 3 (France)
Olivier Siri, CINaM, UMR 7325 CNRS, Aix-Marseille Université, Campus Luminy, case 913, 13288 Marseille Cedex 09 (France)
Search for more papers by this authorO.S. acknowledges the Centre National de la Recherche Scientifique, the Ministère de la Recherche et des Nouvelles Technologies for financial support and PhD grant of Z.C., and Hugues Brisset for the CV recording. D.J. acknowledges the European Research Council (ERC) and the Région des Pays de la Loire for financial support in the framework of a Starting Grant (Marches - 278845) and a recrutement sur poste stratégique, respectively. This research used resources of the GENCI-CINES/IDRIS (Grants c2012085117), the CCIPL (Centre de Calcul Intensif des Pays de Loire), the local Troy cluster acquired thanks to Région des Pays de la Loire.
Graphical Abstract
No pyrrol: Azacalixphyrin (see picture), a novel isostructural and isoelectronic “pyrrol-free” analogue of porphyrins is easily prepared in two straightforward steps. The azacalixphyrin is aromatic, absorbs in the entire visible region, and is highly stable (even in the presence of water under air) owing to its unusual bis-zwitterionic character.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Filename | Description |
---|---|
anie_201301217_sm_miscellaneous_information.pdf2.5 MB | miscellaneous_information |
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.
References
- 1
- 1a Handbook of Porphyrin Science: With Applications to Chemistry, Physics, Materials Science Engineering, Biology and Medicine (Ed.: ), World Scientific Press, Singapore, 2011;
- 1bM. Vinodh, F. H. Alipour, A. A. Mohamod, T. F. Al-Azemi, Molecules 2012, 17, 11763–11799;
- 1cL. L. Li, E. W.-G. Diau, Chem. Soc. Rev. 2013, 42, 291–304;
- 1dW.-D. Jang, Y.-H. Jeong, Supramol. Chem. 2013, 25, 34–40;
- 1eH. Yaku, T. Murashima, D. Miyoshi, N. Sugimoto, Molecules 2012, 17, 10586–10613;
- 1fV. Bulach, F. Sguerra, M. W. Hosseini, Coord. Chem. Rev. 2012, 256, 1468–1478;
- 1gM. J. Griffith, K. Sunahara, P. Wagner, K. Wagner, G. G. Wallace, D. L. Officer, A. Furube, R. Katoh, S. Mori, A. J. Mozer, Chem. Commun. 2012, 48, 4145–4162.
- 2
- 2aE. Vogel, M. Köcher, H. Schmickler, J. Lex, Angew. Chem. 1986, 98, 262–264; Angew. Chem. Int. Ed. Engl. 1986, 25, 257–259;
- 2bD. Sánchez-García, J. L. Sessler, Chem. Soc. Rev. 2008, 37, 215–232;
- 2cE. Vogel, N. Jux, R. Rodriguze-Cal, J. Lex, Angew. Chem. 1990, 102, 1431–1434; Angew. Chem. Int. Ed. Engl. 1990, 29, 1387–1390.
- 3
- 3a Phthalocyanine Molecular Materials, Structure & Bonding (Ed.: ), Springer, Berlin, 2010;
- 3bR. Wu, A. Cetin, W. S. Durfee, C. J. Ziegler, Angew. Chem. 2006, 118, 5798–5801; Angew. Chem. Int. Ed. 2006, 45, 5670–5673;
- 3cA. Çetin, W. S. Durfee, C. J. Ziegler, Inorg. Chem. 2007, 46, 6239–6241;
- 3dS. Sripothongnak, A. M. Pischera, M. P. Espe, W. S. Durfee, C. J. Ziegler, Inorg. Chem. 2009, 48, 1293–1300;
- 3eS. Sripothongnak, N. Barone, C. J. Ziegler, Chem. Commun. 2009, 4584–4586;
- 3fA. Çetin, S. Sripothongnak, M. Kawa, W. S. Durfee, C. J. Ziegler, Chem. Commun. 2007, 4289–4290;
- 3gA. Muranaka, S. Ohira, D. Hashizume, H. Koshino, F. Kyotani, M. Hirayama, M. Uchiyama, J. Am. Chem. Soc. 2012, 134, 190–193;
- 3hT. D. Lash, Angew. Chem. 1995, 107, 2703–2705;
10.1002/ange.19951072210 Google ScholarAngew. Chem. Int. Ed. Engl. 1995, 34, 2533–2535.
- 4
- 4aH. Tsue, K. Ishibashi, R. Tamamura, Topic in Heterocyclic chemistry 2008, 17, 73–96;
- 4bM. Touil, M. Elhabiri, M. Lachkar, O. Siri, Eur. J. Org. Chem. 2011, 1914–1921.
- 5R. Nietzki, E. Hagenbach, Ber. Dtsch. Chem. Ges. 1887, 20, 328–338;
10.1002/cber.18870200181 Google ScholarR. Nietzki, E. Hagenbach, Ber. Dtsch. Chem. Ges. 1887, 20, 2114–2118.10.1002/cber.18870200208 Google Scholar
- 6S. Dähne, D. Leupold, Angew. Chem. 1966, 78, 1029–1039;
10.1002/ange.19660782302 Google ScholarAngew. Chem. Int. Ed. Engl. 1966, 5, 984–993.
- 7O. Siri, P. Braunstein, M. M. Rohmer, M. Bénard, R. Welter, J. Am. Chem. Soc. 2003, 125, 13793–13803.
- 8H. Rumpel, H. H. Limbach, J. Am. Chem. Soc. 1989, 111, 5429–5441.
- 9
- 9aZ. Chen, C. S. Wannere, C. Corminboeuf, R. Puchta, P. R. Schleyer, Chem. Rev. 2005, 105, 3842–3888;
- 9bB. Kiran, M. T. Nguyen, J. Organomet. Chem. 2002, 643–644, 265–271.
- 10A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435–436.
- 11C. P. Gros, L. Jaquinod, R. G. Khoury, M. M. Olmstead, K. M. Smith, J. Porphyrins Phthalocyanines 1997, 1, 201–212.
- 12E. Shirman, A. Ustinov, N. Ben-Shitrit, H. Weissman, M. A. Iron, R. Cohen, B. Rybtchinski, J. Phys. Chem. B 2008, 112, 8855–8858.
- 13
- 13aJ. V. Caspar, T. J. Meyer, J. Phys. Chem. 1983, 87, 952–957;
- 13bC. Goze, J. C. Chambron, V. Heitz, D. Pomeranc, X. J. Salom-Roig, J. P. Sauvage, A. F. Morales, F. Barigelletti, Eur. J. Inorg. Chem. 2003, 3752–3758.
- 14
- 14aD. Jacquemin, B. Mennucci, C. Adamo, Phys. Chem. Chem. Phys. 2011, 13, 16987–16998;
- 14bC. Adamo, D. Jacquemin, Chem. Soc. Rev. 2013, 42, 845–856.
- 15
- 15aN. Sprutta, S. Mackowiak, M. Kocik, L. Szterenberg, T. Lis, L. Latos-Grazynski, Angew. Chem. 2009, 121, 3387–3391;
10.1002/ange.200900496 Google ScholarAngew. Chem. Int. Ed. 2009, 48, 3337–3341;
- 15bE. Vogel, C. Fröde, A. Breihan, H. Schmickler, J. Lex, Angew. Chem. 1997, 109, 2722–2725;
10.1002/ange.19971092312 Google ScholarAngew. Chem. Int. Ed. Engl. 1997, 36, 2609–2612;
- 15cE. Vogel, W. Haas, B. Knipp, J. Lex, H. Schmickler, Angew. Chem. 1988, 100, 445–448; Angew. Chem. Int. Ed. Engl. 1988, 27, 406–409;
- 15dE. Vogel, P. Röhrig, M. Sicken, B. Knipp, A. Herrmann, M. Pohl, H. Schmickler, J. Lex, Angew. Chem. 1989, 101, 1683–1687; Angew. Chem. Int. Ed. Engl. 1989, 28, 1651–1655.
- 16
- 16aG. Qian, Z. Y. Wang, Chem. Asian J. 2010, 5, 1006–1029;
- 16bH. Jiang, Macromol. Rapid Commun. 2010, 31, 2007–2034.
- 17
- 17aO. Siri, J. P. Taquet, J. P. Collin, M. D. Rohmer, M. Bénard, P. Braunstein, Chem. Eur. J. 2005, 11, 7247–7253;
- 17bO. Siri, P. Braunstein, J. P. Taquet, J. P. Collin, R. Welter, Dalton Trans. 2007, 1481–1483.
- 18CCDC 913387 (2⋅2 HCl) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.