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Pure Appl. Chem., 1993, Vol. 65, No. 1, pp. 143-152

http://dx.doi.org/10.1351/pac199365010143

The porphyrins from the 'annulene chemist's' perspective

E. Vogel

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  • Gopalakrishna Tullimilli Y., Reddy J. Sreedhar, Anand Venkataramanarao G.: Antiaromatic Supramolecules: F⋅⋅⋅S, F⋅⋅⋅Se, and F⋅⋅⋅π Intermolecular Interactions in 32 π Expanded Isophlorins. Angew. Chem. 2013, 125, 1807. <http://dx.doi.org/10.1002/ange.201207987>
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  • Gopalakrishna Tullimilli Y., Reddy J. Sreedhar, Anand Venkataramanarao G.: Antiaromatic Supramolecules: F⋅⋅⋅S, F⋅⋅⋅Se, and F⋅⋅⋅π Intermolecular Interactions in 32 π Expanded Isophlorins. Angew. Chem. Int. Ed. 2013, 52, 1763. <http://dx.doi.org/10.1002/anie.201207987>
  • Sakow Dimitri, Böker Birte, Brandhorst Kai, Burghaus Olaf, Bröring Martin: 10-Heterocorroles: Ring-Contracted Porphyrinoids with Fine-Tuned Aromatic and Metal-Binding Properties. Angew. Chem. Int. Ed. 2013, 52, 4912. <http://dx.doi.org/10.1002/anie.201300757>
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  • Makino Masakazu, Aihara Jun-ichi: Macrocyclic Aromaticity of Porphyrin Units in Fully Conjugated Oligoporphyrins. J. Phys. Chem. A 2012, 116, 8074. <http://dx.doi.org/10.1021/jp304681h>
  • Aihara Jun-ichi, Nakagami Yuto, Sekine Rika, Makino Masakazu: Validity and Limitations of the Bridged Annulene Model for Porphyrins. J. Phys. Chem. A 2012, 116, 11718. <http://dx.doi.org/10.1021/jp310480d>
  • Sung Young Mo, Pacholska-Dudziak Ewa, Latos-Grażyński Lechosław, Kim Dongho: The role of nitrogen bridges perturbing the photophysical properties in the porphyrin framework. Chem. Commun. 2012, 48, 8643. <http://dx.doi.org/10.1039/c2cc34287a>
  • Arnold Lena, Baumgarten Martin, Müllen Klaus: A carbazole-containing porphyrinoid: synthesis and oxidation to the porphyrin-state. Chem. Commun. 2012, 48, 9640. <http://dx.doi.org/10.1039/c2cc35550g>
  • Nakagami Yuto, Sekine Rika, Aihara Jun-ichi: The origin of global and macrocyclic aromaticity in porphyrinoids. Org. Biomol. Chem. 2012, 10, 5219. <http://dx.doi.org/10.1039/c2ob25692d>
  • Lash Timothy D.: Carbaporphyrins, porphyrin isomers and the legacy of Emanuel Vogel. J. Porphyrins Phthalocyanines 2012, 16, 423. <http://dx.doi.org/10.1142/S1088424612300017>
  • Vargas-Zúñiga Gabriela I., Roznyatovskiy Vladimir V., Nepomnyaschii Alexander, Lynch Vincent M., Sessler Jonathan L.: π-Metal complexes of i-propyldinaphthoporphycene. J. Porphyrins Phthalocyanines 2012, 16, 479. <http://dx.doi.org/10.1142/S1088424612500472>
  • Stępień Marcin, Sprutta Natasza, Latos-Grażyński Lechosław: Figure-Eight-Strukturen, Möbius-Bänder und mehr: Konformation und Aromatizität von Porphyrinoiden. Angew. Chem. 2011, 123, 4376. <http://dx.doi.org/10.1002/ange.201003353>
  • Senge Mathias O.: Extrovertierte Verwirrung - Linus Pauling, Melvin Calvin und Porphyrinisomere. Angew. Chem. 2011, 123, 4360. <http://dx.doi.org/10.1002/ange.201003660>
  • Bröring Martin: Wie beschreibt man Aromatizität bei Porphyrinoiden?. Angew Chem 2011, 123, 2484. <http://dx.doi.org/10.1002/ange.201007442>
  • Vogel Emanuel: Von kleinen Kohlenstoffringen zu Porphyrinen - ein persönlicher Bericht über 50 Jahre Forschung. Angew. Chem. 2011, 123, 4366. <http://dx.doi.org/10.1002/ange.201101347>
  • Altenbach Hans-Josef: Emanuel Vogel (1927-2011). angew chemie 2011, 123, 6833. <http://dx.doi.org/10.1002/ange.201103222>
  • Stępień Marcin, Sprutta Natasza, Latos-Grażyński Lechosław: Figure Eights, Möbius Bands, and More: Conformation and Aromaticity of Porphyrinoids. Angew. Chem. Int. Ed. 2011, 50, 4288. <http://dx.doi.org/10.1002/anie.201003353>
  • Senge Mathias O.: Extroverted Confusion-Linus Pauling, Melvin Calvin, and Porphyrin Isomers. Angew. Chem. Int. Ed. 2011, 50, 4272. <http://dx.doi.org/10.1002/anie.201003660>
  • Bröring Martin: How Should Aromaticity Be Described in Porphyrinoids?. Angew Chem Int Ed 2011, 50, 2436. <http://dx.doi.org/10.1002/anie.201007442>
  • Vogel Emanuel: From Small Carbocyclic Rings to Porphyrins: A Personal Account of 50 Years of Research. Angew. Chem. Int. Ed. 2011, 50, 4278. <http://dx.doi.org/10.1002/anie.201101347>
  • Altenbach Hans-Josef: Emanuel Vogel (1927-2011). Angew Chem Int E 2011, 50, 6701. <http://dx.doi.org/10.1002/anie.201103222>
  • Pacholska-Dudziak Ewa, Szterenberg Ludmiła, Latos-Grażyński Lechosław: A Flexible Porphyrin-Annulene Hybrid: A Nonporphyrin Conformation formeso-Tetraaryldivacataporphyrin. Chem Eur J 2011, 17, 3500. <http://dx.doi.org/10.1002/chem.201002765>
  • Kuzuhara Daiki, Yamada Hiroko, Yano Keiko, Okujima Tetsuo, Mori Shigeki, Uno Hidemitsu: First Synthesis of Dodecasubstituted Porphycenes. Chem Eur J 2011, 17, 3376. <http://dx.doi.org/10.1002/chem.201002788>
  • Kuzuhara Daiki, Yamada Hiroko, Mori Shigeki, Okujima Tetsuo, Uno Hidemitsu: Synthesis, structures and properties of benzoporphycenes and naphthoporphycenes. J. Porphyrins Phthalocyanines 2011, 15, 930. <http://dx.doi.org/10.1142/S1088424611003823>
  • VOGEL E.: ChemInform Abstract: The Porphyrins from the ′Annulene Chemist′s′ Perspective. ChemInform 2010, 24, no. <http://dx.doi.org/10.1002/chin.199316327>
  • Makino Masakazu, Aihara Jun-ichi: Prediction of the main macrocyclic conjugation pathway for porphyrinoids from the ring current distribution. Org Biomol Chem 2010, 8, 261. <http://dx.doi.org/10.1039/b910521b>
  • Kuzuhara Daiki, Mack John, Yamada Hiroko, Okujima Tetsuo, Ono Noboru, Kobayashi Nagao: Synthesis, Structures, and Optical and Electrochemical Properties of Benzoporphycenes. Chem Eur J 2009, 15, 10060. <http://dx.doi.org/10.1002/chem.200900755>
  • Aihara Jun-ichi, Makino Masakazu: Macrocyclic conjugation in N-fused porphyrins and related species. J Mol Model 2009, 15, 1427. <http://dx.doi.org/10.1007/s00894-009-0508-z>
  • Pacholska-Dudziak Ewa, Latos-Grażyński Lechosław: Aza-deficient porphyrin as a ligand. Coord Chem Rev - 2009, 253, 2036. <http://dx.doi.org/10.1016/j.ccr.2009.01.029>
  • Aihara Jun-ichi, Horibe Hideki: Macrocyclic aromaticity in Hückel and Möbius conformers of porphyrinoids. Org Biomol Chem 2009, 7, 1939. <http://dx.doi.org/10.1039/b901621j>
  • Aihara Jun-ichi, Makino Masakazu: Aromaticity and Conjugation in Sapphyrin and Orangarin. Bull Chem Soc Jpn 2009, 82, 675. <http://dx.doi.org/10.1246/bcsj.82.675>
  • Jux Norbert: Der Porphyrin-Twist: Hückel- und Möbius-Aromatizität. Angew Chem 2008, 120, 2577. <http://dx.doi.org/10.1002/ange.200705568>
  • Jux Norbert: The Porphyrin Twist: Hückel and Möbius Aromaticity. Angew Chem Int Ed 2008, 47, 2543. <http://dx.doi.org/10.1002/anie.200705568>
  • Ye Shengfa, Tuttle Tell, Bill Eckhard, Simkhovich Liliya, Gross Zeev, Thiel Walter, Neese Frank: The Electronic Structure of Iron Corroles: A Combined Experimental and Quantum Chemical Study. Chem Eur J 2008, 14, 10839. <http://dx.doi.org/10.1002/chem.200801265>
  • Xiang Mei, Yao Guo-Hua, Lu Tong-Tong, He Tian-Jing, Chen Dong-Ming, Tomura Masaaki, Wahab Hilal S., Bredow Thomas, Aliwi Salah M.: Density functional theory study on the dynamic Jahn-Teller effect of tetraoxaporphyrin cation and anion radicals. Journal of Molecular Structure: THEOCHEM 2008, 868, 6. <http://dx.doi.org/10.1016/j.theochem.2008.07.041>
  • Sánchez-García David, Sessler Jonathan L.: Porphycenes: synthesis and derivatives. Chem Soc Rev 2008, 37, 215. <http://dx.doi.org/10.1039/b704945e>
  • Aihara Jun-ichi, Kimura Eiichi, Krygowski Tadeusz Marek: Aromatic Conjugation Pathways in Porphyrins. Bull Chem Soc Jpn 2008, 81, 826. <http://dx.doi.org/10.1246/bcsj.81.826>
  • Podstawka Edyta, Fościak Mateusz, Chmielewski Piotr, Proniewicz Leonard M.: Vibrational analysis of Ni(II) complex with 4,12-ditolyl-16,24-diphenyl-3-thiaporphyrin (SDTDPPNi(II)Cl) and its isotopic labeled (61Ni(II), −d6, and −d10) derivatives. J. Porphyrins Phthalocyanines 2007, 11, 652. <http://dx.doi.org/10.1142/S108842460700076X>
  • Senge Mathias O., Sergeeva Natalia N.: “Metamorphose” von Tetrapyrrolmakrocyclen. Angew Chem 2006, 118, 7654. <http://dx.doi.org/10.1002/ange.200603249>
  • Senge Mathias O., Sergeeva Natalia N.: Metamorphosis of Tetrapyrrole Macrocycles. Angew Chem Int Ed 2006, 45, 7492. <http://dx.doi.org/10.1002/anie.200603249>
  • Gulam Rabbani M., Neya Saburo, Teraoka Junji: Resonance Raman spectra of highly reduced iron porphycenes. J. Porphyrins Phthalocyanines 2006, 10, 1271. <http://dx.doi.org/10.1142/S1088424606000648>
  • Dobkowski Jacek, Lobko Yauheni, Gawinkowski Sylwester, Waluk Jacek: Energy relaxation paths in matrix-isolated excited molecules: Comparison of porphycene with dibenzoporphycenes. chem phys letts 2005, 416, 128. <http://dx.doi.org/10.1016/j.cplett.2005.09.043>
  • Hayashi Takashi, Nakashima Yuji, Ito Kazuyuki, Ikegami Takahiro, Aritome Isao, Suzuki Akihiro, Hisaeda Yoshio: Synthesis, Structure, and Chemical Property of the First Fluorine-Containing Porphycene. Org Lett 2003, 5, 2845. <http://dx.doi.org/10.1021/ol0348452>
  • Ghosh Abhik, Moulder John, Bröring Martin, Vogel Emanuel: X-Ray Photoelectron Spectroscopy of Porphycenes: Charge Asymmetry Across Low-Barrier Hydrogen Bonds. Angew Chem 2001, 113, 445. <http://dx.doi.org/10.1002/1521-3757(20010119)113:2<445::AID-ANGE445>3.0.CO;2-F>
  • Sprutta Natasza, Latos-Grażyński Lechosław: Figure-Eight Tetrathiaoctaphyrin and Dihydrotetrathiaoctaphyrin. Chem Eur J 2001, 7, 5099. <http://dx.doi.org/10.1002/1521-3765(20011203)7:23<5099::AID-CHEM5099>3.0.CO;2-M>
  • Ghosh Abhik, Moulder John, Bröring Martin, Vogel Emanuel: X-Ray Photoelectron Spectroscopy of Porphycenes: Charge Asymmetry Across Low-Barrier Hydrogen Bonds. Angew Chem Int Ed 2001, 40, 431. <http://dx.doi.org/10.1002/1521-3773(20010119)40:2<431::AID-ANIE431>3.0.CO;2-A>
  • Wojaczyński Jacek, Latos-Grażyński Lechosław: Poly- and oligometalloporphyrins associated through coordination. Coord Chem Rev - 2000, 204, 113. <http://dx.doi.org/10.1016/S0010-8545(99)00207-6>
  • Märkl Gottfried, Ehrl Robert, Kreitmeier Peter, Burgemeister Thomas: 8,19-Dimethyl-tetraepoxy[22]annulen(2.1.2.1): ein erstes Tetraepoxy-Verbrücktes aromatisches [22]Annulen. HCA 1998, 81, 93. <http://dx.doi.org/10.1002/hlca.19980810111>
  • Märkl Gottfried, Sauer Heinrich, Stiegler Jürgen, Kreitmeier Peter, Burgemeister Thomas: Tetraepoxy[22]annulen(2.2.2.0): Ein neuartiges Tetraepoxy-verbrücktes, neutrales, aromatisches [22]Annulen. HCA 1998, 81, 1077. <http://dx.doi.org/10.1002/hlca.19980810521>
  • Märkl Gottfried, Knott Th., Kreitmeier Peter, Burgemeister Thomas, Kastner F.: Makrocyclische [4n + 2]-Hückel-Aromaten bisn = 9 und [4n]-Antiaromaten bisn = 10: Homologe Reihen vom Tetraepoxy[24]-annulen(2.0.2.0) zum Tetraepoxy[40]annulen(12.0.12.0) und vom ‘Tetraoxa-[22]porphyrin(2.0.2.0)’-zum ‘Tetraepoxa[38]porphyrin(12.0.12.0)’-Dikation. HCA 1998, 81, 1480. <http://dx.doi.org/10.1002/hlca.19980810553>
  • Vogel Emanuel, Bröring Martin, Erben Christoph, Demuth Ralf, Lex Johann, Nendel Maja, Houk Kendall N.: Palladiumkomplexe der neuen Porphyrinisomere (Z)- und (E)-Isoporphycen – PdII-induzierte Cyclisierungen von Tetrapyrrolaldehyden. Angew Chem 1997, 109, 363. <http://dx.doi.org/10.1002/ange.19971090409>
  • Vogel Emanuel, Bröring Martin, Weghorn Steven J., Scholz Peter, Deponte Reiner, Lex Johann, Schmickler Hans, Schaffner Kurt, Braslavsky Silvia E., Müller Martin: Octaethylhemiporphycen: Synthese, Molekülstruktur und Photophysik. Angew Chem 1997, 109, 1725. <http://dx.doi.org/10.1002/ange.19971091525>
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  • Vogel Emanuel, Fröde Christoph, Breihan Andreas, Schmickler Hans, Lex Johann: Octaethyltetraselenaporphyrin-Dikation. Angew Chem 1997, 109, 2722. <http://dx.doi.org/10.1002/ange.19971092312>
  • Chmielewski Piotr J., Latos-Grażyński Lechoslaw, Olmstead Marilyn M., Balch Alan L.: Nickel Complexes of 21-Oxaporphyrin and 21, 23-Dioxaporphyrin. Chem. Eur. J. 1997, 3, 268. <http://dx.doi.org/10.1002/chem.19970030216>
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  • Birklund-Andersen Kristine, Vogel Emanual, Waluk Jacek: Electronic transition moment directions and tautomerization of 9,10,19,20-tetra-n-propylporphycene. chem phys letts 1997, 271, 341. <http://dx.doi.org/10.1016/S0009-2614(97)00460-0>
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