Hemiporphycene from the Expansion of a Corrole Ring
2005; Wiley; Volume: 44; Issue: 20 Linguagem: Inglês
10.1002/anie.200500481
ISSN1521-3773
AutoresRoberto Paolesse, Sara Nardis, Manuela Stefanelli, Frank R. Fronczek, M. Graça H. Vicente,
Tópico(s)Photosynthetic Processes and Mechanisms
ResumoAngewandte Chemie International EditionVolume 44, Issue 20 p. 3047-3050 Communication Hemiporphycene from the Expansion of a Corrole Ring† Roberto Paolesse Prof. Dr., Roberto Paolesse Prof. Dr. [email protected] Dipartimento di Scienze e Tecnologie Chimiche, Università di Roma "Tor Vergata" and CNR-IMM, 00133 Roma, Italy, Fax: (+39) 067-259-4328Search for more papers by this authorSara Nardis Dr., Sara Nardis Dr. Dipartimento di Scienze e Tecnologie Chimiche, Università di Roma "Tor Vergata", 00133 Roma, ItalySearch for more papers by this authorManuela Stefanelli, Manuela Stefanelli Dipartimento di Scienze e Tecnologie Chimiche, Università di Roma "Tor Vergata", 00133 Roma, ItalySearch for more papers by this authorFrank R. Fronczek Prof. Dr., Frank R. Fronczek Prof. Dr. Department of Chemistry, Lousiana State University, Baton Rouge, LA 70803, USASearch for more papers by this authorMaria Graça H. Vicente Prof. Dr., Maria Graça H. Vicente Prof. Dr. Department of Chemistry, Lousiana State University, Baton Rouge, LA 70803, USASearch for more papers by this author Roberto Paolesse Prof. Dr., Roberto Paolesse Prof. Dr. [email protected] Dipartimento di Scienze e Tecnologie Chimiche, Università di Roma "Tor Vergata" and CNR-IMM, 00133 Roma, Italy, Fax: (+39) 067-259-4328Search for more papers by this authorSara Nardis Dr., Sara Nardis Dr. Dipartimento di Scienze e Tecnologie Chimiche, Università di Roma "Tor Vergata", 00133 Roma, ItalySearch for more papers by this authorManuela Stefanelli, Manuela Stefanelli Dipartimento di Scienze e Tecnologie Chimiche, Università di Roma "Tor Vergata", 00133 Roma, ItalySearch for more papers by this authorFrank R. Fronczek Prof. Dr., Frank R. Fronczek Prof. Dr. Department of Chemistry, Lousiana State University, Baton Rouge, LA 70803, USASearch for more papers by this authorMaria Graça H. Vicente Prof. Dr., Maria Graça H. Vicente Prof. Dr. Department of Chemistry, Lousiana State University, Baton Rouge, LA 70803, USASearch for more papers by this author First published: 09 May 2005 https://doi.org/10.1002/anie.200500481Citations: 46 † This work was supported by the MIUR-FIRB (Italy; project RBNE01KZZM). 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 Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Formation of the vinylogous bridge between adjacent pyrrole rings (A and B) in the reaction of 5,10,15-triphenylcorrole with CI4 affords the corresponding hemiporphycene (see structure; N blue, I pink, C white, H green). This approach allows a facile preparation of functionalized hemiporphycenes. References 1 1aJ.-H. Chou, H. S. Nalwa, M. E. Kosal, N. A. Rakow, K. Suslick in The Porphyrin Handbook, Vol. 6 (Eds: ), Academic Press, New York, 2000, p. 43; 1bR. K. Pandey, G. Zheng in The Porphyrin Handbook, Vol. 6 (Eds: ), Academic Press, New York, 2000, p. 157; 1cT. Malinski in The Porphyrin Handbook, Vol. 6 (Eds: ), Academic Press, New York, 2000, p. 231. 2 2aJ. L. Sessler, A. Gebauer, E. Vogel in The Porphyrin Handbook, Vol. 2 (Eds: ), Academic Press, New York, 2000, p. 1; 2bJ. L. Sessler, A. Gebauer, S. J. Weghorn in The Porphyrin Handbook, Vol. 2 (Eds: ), Academic Press, New York, 2000, p. 55. 3 3aD. Mansuy, P. Battioni in The Porphyrin Handbook, Vol. 4 (Eds: ), Academic Press, New York, 2000, p. 1; 3bD. Gust, T. A. Moore in The Porphyrin Handbook, Vol. 8 (Eds: ), Academic Press, New York, 2000, p. 153. 4A. W. Johnson, I. T. Kay, J. Chem. Soc. 1965, 1620. 5C. Erben, S. Will, K. M. Kadish in The Porphyrin Handbook, Vol. 2 (Eds: ), Academic Press, New York, 2000, p. 233. 6A. Mahammed, H. B. Gray, A. E. Meier-Callahan, Z. Gross, J. Am. Chem. Soc. 2003, 125, 1162. 7F. A. Walker, Inorg. Chem. 2003, 42, 4526. 8 8aR. Paolesse in The Porphyrin Handbook, Vol. 2 (Eds: ), Academic Press, New York, 2000, p. 201; 8bD. T. Gryko, Eur. J. Org. Chem. 2002, 11, 1735. 9S. Nardis, D. Monti, R. Paolesse, Mini-Reviews in Organic Chemistry, Bentham Science Publishers Ltd., San Francisco (USA), in press. 10R. Paolesse, L. Jaquinod, M. O. Senge, K. M. Smith, J. Org. Chem. 1997, 62, 6193. 11R. Paolesse, S. Nardis, M. Venanzi, M. Mastroianni, M. Russo, F. R. Fronczek, M. G. Vicente, Chem. Eur. J. 2003, 9, 1192. 12A solution of 5,10,15-triphenylcorrole 1 (45 mg, 0.085 mmol), carbon tetraiodide (45 mg, 0.087 mmol), and DMF (0.9 mL, 11.6 mmol) in CH2Cl2 (50 mL) was heated at reflux for 1 h. The progress of the reaction was monitored by UV/Vis spectroscopy and by TLC. After disappearance of the starting material, the crude mixture was washed with water and a solution of NaHCO3, and the solvent was evaporated under vacuum. Chromatography on silica gel using CH2Cl2 as the eluent afforded a green band as the major product, which, after crystallization from CH2Cl2/hexane, gave red–violet crystals of 2 (17 mg, 30 %). UV/Vis (CH2Cl2): λmax (log ε): 419 (5.28), 522 (3.8), 563 (4.15), 591 (4.02), 637 nm (4.03); 1H NMR (400 MHz, CDCl3, J [Hz]): δ=9.37 (d, 1 H, J=4.4, β-pyrrolic), 9.14 (d, 1 H, J=4.4, β-pyrrolic), 9.05 (d, 1 H, J=4.5, β-pyrrolic), 8.75 (d, 1 H, J=4.5, β-pyrrolic), 8.50 (d, 1 H, J=4.4, β-pyrrolic), 8.20 (d, 3 H, J=6.6, phenyl), 8.09 (d, 1 H, J=4.4, β-pyrrolic), 8.03 (d, 2 H, J=7.1, β-pyrrolic), 7.77(m, 7 H, phenyl), 7.65 ppm (m, 5 H, phenyl); MS (FAB): m/z (%): 664 (100), 538 (60). 13Single crystals of 2, C38H25N4I, were obtained by slow diffusion of hexane into a solution of 2 in CH2Cl2. The unit cell was monoclinic, space group P21/c, a=24.637(5), b=10.172(3), c=24.663(6) Å, β=112.186(8)°, V=5723(2) Å3, Z=8, ρcalcd=1.542 g cm−3, μMo=1.155 mm−1, R=0.079 (8718 data with F2>2σF2), Rw=0.192 (all 13 574 unique data), and 775 refined parameters. A total of 39 732 data were collected at T=100 K to θ=28.3° with MoKα radiation (λ=0.71073 Å) on a Nonius KappaCCD diffractometer using a green blade crystal of dimensions 0.37×0.12×0.05 mm3. Absorption corrections were carried out by a multiscan method using HKL Scalepack, with transmission coefficients 0.714–0.943. Refinement was by full-matrix least squares using SHELXL, with hydrogen atoms in idealized positions. There are two independent molecules in the asymmetric unit. CCDC-258645 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. 14H. J. Callot, A. Rohrer, Th. Tschamber, New J. Chem. 1995, 19, 155. 15E. Vogel, M. Bröring, S. J. Weghorn, P. Scholz, R. Deponte, J. Lex, H. Schrnickler, K. Schaffner, S. E. Braslavsky, M. Müller, S. Pörting, C. J. Fowler, J. L. Sessler, Angew. Chem. 1997, 109, 1725; Angew. Chem. Int. Ed. Engl. 1997, 36, 1651. 16H. J. Callot, Th. Tschamber, J. Am. Chem. Soc. 1975, 97, 6175. Citing Literature Volume44, Issue20May 13, 2005Pages 3047-3050 ReferencesRelatedInformation
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