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Pure Appl. Chem., 1990, Vol. 62, No. 3, pp. 557-564

http://dx.doi.org/10.1351/pac199062030557

Novel porphyrinoids

E. Vogel

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  • AbuSalim Deyaa I., Lash Timothy D.: Aromatic character and relative stability of neo-confused porphyrin tautomers and related compounds. Org. Biomol. Chem. 2013, 11, 8306. <http://dx.doi.org/10.1039/c3ob42063a>
  • 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>
  • Saha Mithu, Pal Amarta Kumar, Nandi Shibaji: Pd(0) NPs: a novel and reusable catalyst for the synthesis of bis(heterocyclyl)methanes in water. RSC Adv. 2012, 2, 6397. <http://dx.doi.org/10.1039/c2ra20445b>
  • 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>
  • Czerski Igor, Listkowski Arkadiusz, Nawrocki Jan, Urbańska Natalia, Piwoński Hubert, Sokołowski Adam, Pietraszkiewicz Oksana, Pietraszkiewicz Marek, Waluk Jacek: The long and winding road to new porphycenes. J. Porphyrins Phthalocyanines 2012, 16, 589. <http://dx.doi.org/10.1142/S1088424612500733>
  • 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>
  • 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>
  • Singh Kamaljit, Sharma Shivali, Sharma Amit: Unique versatility of Amberlyst 15. An acid and solvent-free paradigm towards synthesis of bis(heterocyclyl)methane derivatives. Journal of Molecular Catalysis A 2011, 347, 34. <http://dx.doi.org/10.1016/j.molcata.2011.07.007>
  • Scharf Austin B., Betley Theodore A.: Electronic Perturbations of Iron Dipyrrinato Complexes via Ligand β-Halogenation and meso-Fluoroarylation. Inrog Chem 2011, 50, 6837. <http://dx.doi.org/10.1021/ic2009539>
  • Singh Kamaljit, Sharma Shivali, Sharma Amit: Efficient Synthesis of Bis(heterocyclyl)methanes. Synth Common 2011, 41, 3491. <http://dx.doi.org/10.1080/00397911.2010.518330>
  • Sprutta Natasza, Maćkowiak Stanisław, Kocik Marzena, Szterenberg Ludmiła, Lis Tadeusz, Latos-Grażyński Lechosław: Tetraazuliporphyrin Tetracation. Angew Chem 2009, 121, 3387. <http://dx.doi.org/10.1002/ange.200900496>
  • Sprutta Natasza, Maćkowiak Stanisław, Kocik Marzena, Szterenberg Ludmiła, Lis Tadeusz, Latos-Grażyński Lechosław: Tetraazuliporphyrin Tetracation. Angew Chem Int Ed 2009, 48, 3337. <http://dx.doi.org/10.1002/anie.200900496>
  • 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>
  • Cuesta Luciano, Karnas Elizabeth, Lynch Vincent M., Chen Ping, Shen Jing, Kadish Karl M., Ohkubo Kei, Fukuzumi Shunichi, Sessler Jonathan L.: Metalloporphycenes: Synthesis and Characterization of (Pentamethylcyclopentadienyl)ruthenium Sitting-Atop and π-Complexes. J Am Chem Soc 2009, 131, 13538. <http://dx.doi.org/10.1021/ja905284d>
  • Singh Kamaljit, Sharma Amit: Selective lithiation of bis(furan-2-yl)methane: an efficient protocol for novel meso-functionalised synthons. Tetrahetron Lett 2008, 49, 6234. <http://dx.doi.org/10.1016/j.tetlet.2008.08.040>
  • Sánchez-García David, Sessler Jonathan L.: Porphycenes: synthesis and derivatives. Chem Soc Rev 2008, 37, 215. <http://dx.doi.org/10.1039/b704945e>
  • 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>
  • Lang K., Mosinger J., Wagnerová D.M.: Photophysical properties of porphyrinoid sensitizers non-covalently bound to host molecules; models for photodynamic therapy. Coord Chem Rev - 2004, 248, 321. <http://dx.doi.org/10.1016/j.ccr.2004.02.004>
  • 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>
  • Eckert Anke, Pritzkow Hans, Siebert Walter: Synthesis and Structure of Diboraporphyrinogenes. Eur J Inorg Chem 2002, 2002, 2064. <http://dx.doi.org/10.1002/1099-0682(200208)2002:8<2064::AID-EJIC2064>3.0.CO;2-4>
  • 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>
  • Carré Francis H., Corriu Robert J.-P., Deforth Thomas, Douglas William E., Siebert Walter S., Weinmann Wolfgang: Ein borverbrücktes Tetrathiaporphyrinogen. Angew Chem 1998, 110, 654. <http://dx.doi.org/10.1002/(SICI)1521-3757(19980302)110:5<654::AID-ANGE654>3.0.CO;2-C>
  • Toledano H., Edrei R., Kimel S.: Photodynamic damage by liposome-bound porphycenes: comparison between in vitro and in vivo models. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY 1998, 42, 20. <http://dx.doi.org/10.1016/S1011-1344(97)00110-3>
  • 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>
  • GUILARD ROGER, PICHON-PESME VIRGINIE, LACHEKAR HASSANE, LECOMTE CLAUDE, AUKAULOO ALLY M., BOULAS PIERRE L., KADISH KARL M.: Synthesis and Electrochemistry of Aluminum Porphycenes: Crystal and Molecular Structure of Methyl-σ-Bonded Aluminum Etioporphycene. J. Porphyrins Phthalocyanines 1997, 01, 109. <http://dx.doi.org/10.1002/(SICI)1099-1409(199704)1:2<109::AID-JPP13>3.0.CO;2-4>
  • 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>
  • Zandler Melvin E., D'Souza Francis: Electronic and structural properties of the metalloporphyrin structural isomers: semiempirical AM1 and PM3 calculations. Journal of Molecular Structure: THEOCHEM 1997, 401, 301. <http://dx.doi.org/10.1016/S0166-1280(97)00022-5>
  • Wu Yun-Dong, Chan Kyle W.K.: Geometrical and electronic properties of dibenzoporphycenes. Journal of Molecular Structure: THEOCHEM 1997, 398-399, 325. <http://dx.doi.org/10.1016/S0166-1280(97)00040-7>
  • Braslavsky Silvia E., Müller Martin, Mártire Daniel O., Pörting Sigrid, Bertolotti Sonia G., Chakravorti Sankar, Koç-Weier Gül, Knipp Bernd, Schaffner Kurt: Photophysical properties of porphycene derivatives (18 π porphyrinoids). JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY 1997, 40, 191. <http://dx.doi.org/10.1016/S1011-1344(97)00075-4>
  • Iyoda Masahiko, Kondo Terumasa, Okabe Toshitaka, Matsuyama Haruo, Sasaki Shigeru, Kuwatani Yoshiyuki: A Simple and Efficient Synthesis of Di-, Tri-, and Tetraferrocenylarenes. Chem Lett 1997, 35. <http://dx.doi.org/10.1246/cl.1997.35>
  • Kurata Hiroyuki, Baba Hiroshige, Oda Masaji: 5, 8, 17, 20-Tetrakis(3, 5-di-t-butylphenyl)-6, 7, 18, 19-tetradehydrotetrathia(24)annulene-(4. 0. 4. 0) and Its Dianion: New Thiophene-Derived Paratropic and Diatropic Annulenes. Chem Lett 1997, 571. <http://dx.doi.org/10.1246/cl.1997.571>
  • Vogel Emanuel, Pohl Michael, Herrmann Adalbert, Wiß Torsten, König Christoph, Lex Johann, Gross Maurice, Gisselbrecht Jean Paul: Porphyrinoide Makrocyclen auf Thiophen-Basis: Octaethyltetrathiaporphyrin-Dikation. Angew Chem 1996, 108, 1677. <http://dx.doi.org/10.1002/ange.19961081345>
  • Sessler Jonathan L., Brucker Eric A., Lynch Vincent, Choe Michael, Sorey Steven, Vogel Emanuel: Solution Phase and Single Crystal Diffraction X-ray Analyses of Diprotonated Porphyrin Isomers—Etioporphyrin, Etioporphycene, and Etiocorrphycene Bishydroperchlorate Salts. Chem Eur J 1996, 2, 1527. <http://dx.doi.org/10.1002/chem.19960021209>
  • Vogel Emanuel: Novel porphyrinoid macrocycles and their metal complexes. J Heterocyclic Chem 1996, 33, 1461. <http://dx.doi.org/10.1002/jhet.5570330505>
  • Märkl Gottfried, Hafner Markus, Kreitmeier Peter, Burgemeister Thomas, Kastner Fritz, Porsch Michael, Daub Jörg: Tetraoxa [24] porphyrinogen(4.0.4.0)/tetraoxa[22]porphyrin(4.0.4.0) dication a further isomer of the aromatic 22π-tetraoxaporphyrins. Tetrahedron 1996, 52, 1981. <http://dx.doi.org/10.1016/0040-4020(95)01041-6>
  • Franck Burchard, Nonn Ansgar: Neuartige Porphyrinoide für Chemie und Medizin durch biomimetische Synthesen. Angew Chem 1995, 107, 1941. <http://dx.doi.org/10.1002/ange.19951071704>
  • Vogel Emanuel, Bröring Martin, Fink Jürgen, Rosen Daniel, Schmickler Hans, Lex Johann, Chan Kyle W. K., Wu Yun-Dong, Nendel Maja, Plattner Dietmar A.: Von Porphyrin-Isomeren zu octapyrrolischen Makrocyclen mit 8er-Konformation. Angew Chem 1995, 107, 2705. <http://dx.doi.org/10.1002/ange.19951072211>
  • Gross M., Jux N., Vogel E., Bernard C., Gisselbrecht J.P.: Redox properties of novel tetrapyrroles: Expanded porphycenes. Journal of Electroanalytical Chemistry 1995, 381, 159. <http://dx.doi.org/10.1016/0022-0728(94)03691-U>
  • Qiao Greg GuangHua, Wentrup Curt: 3-carbonyl-3H-indole: Direct observation and tetramerization to a tetrabenzoporphyrin analogue. Tetrahetron Lett 1995, 36, 3913. <http://dx.doi.org/10.1016/0040-4039(95)00640-X>
  • Kawase Takeshi, Darabi Hossein Reza, Uchimiya Rika, Oda Masaji: Synthesis of 5,6,17,18-Bisdehydrotetrathia(24)annulene(2.2.2.2). A Strained Planar Annulene Devoid of Peripheral Conjugation. Chem Lett 1995, 499. <http://dx.doi.org/10.1246/cl.1995.499>
  • Berlin Kurt, Breitmaier Eberhard: Neue Pyridin enthaltende porphyrinoide Makrocyclen. Angew Chem 1994, 106, 229. <http://dx.doi.org/10.1002/ange.19941060226>
  • Lausmann Michael, Zimmer Ingeborg, Lex Johann, Vogel Emanuel, Lueken Heiko, Wieghardt Karl: μ-Oxodieisen(III)-Komplexe von Porphycenen. Angew Chem 1994, 106, 776. <http://dx.doi.org/10.1002/ange.19941060709>
  • Sessler Jonathan L.: Neue Porphyrinisomere. Angew Chem 1994, 106, 1410. <http://dx.doi.org/10.1002/ange.19941061307>
  • Sessler Jonathan L., Brucker Eric A., Weghorn Steven J., Kisters Michael, Schäfer Martin, Lex Johann, Vogel Emanuel: Corrphycen: ein neues Porphyrinisomer. Angew Chem 1994, 106, 2402. <http://dx.doi.org/10.1002/ange.19941062223>
  • Sessler Jonathan L.: New Porphyrin Isomers. Angew Chem Int Ed Engl 1994, 33, 1348. <http://dx.doi.org/10.1002/anie.199413481>
  • Zhongying Hu, Michael Cava P.: Tetrathia[22]annulene[2,1,2,1]. A new thiophene-derived aromatic macrocycle. Tetrahetron Lett 1994, 35, 3493. <http://dx.doi.org/10.1016/S0040-4039(00)73218-7>
  • Che Chi-Ming, Cheung Kung-Kai, Li Zao-Ying, Wong Kwok-Yin, Wang Chih-Chieh, Wang Yu: X-ray crystal structure of [2,7,12,17-tetrapropylporphycenato]platinum(II). A comparison of nickel(II) and platinum(II) porphycene. J Polyhedron 1994, 13, 2563. <http://dx.doi.org/10.1016/S0277-5387(00)83100-9>
  • Vogel Emanuel: Porphyrins Based on Thiophene. Phosphorus Sulfur Silicon Relat Elem 1994, 95, 509. <http://dx.doi.org/10.1080/10426509408034297>
  • Vogel Emanuel, Koch Peter, Hou Xue-Long, Lex Johann, Lausmann Michael, Kisters Michael, Aukauloo Mohamed Ally, Richard Philippe, Guilard Roger: Neue Porphycen-Liganden: Octaethyl- und Etioporphycen (OEPc bzw. EtioPc) — vier- und fünffach koordinierte Zinkkomplexe von OEPc. Angew Chem 1993, 105, 1670. <http://dx.doi.org/10.1002/ange.1761051113>
  • Märkl Gottfried, Striebl Ulrich: Porphyrinoide [22]Annulenochinone. Angew Chem 1993, 105, 1387. <http://dx.doi.org/10.1002/ange.19931050924>
  • Märkl Gottfried, Striebl Ulrich: Porphyrin-Like [22]Annulenoquinones. Angew Chem Int Ed Engl 1993, 32, 1333. <http://dx.doi.org/10.1002/anie.199313331>
  • Miller Douglas C., Johnson Martin R., Becker John J., Ibers James A.: Synthesis and characterization of the new 22-π aromatic furan-containing macrocycle, “ozaphyrin”. J Heterocyclic Chem 1993, 30, 1485. <http://dx.doi.org/10.1002/jhet.5570300604>
  • Hamacher V., Plato M., Möbius K., Vogel E.: EPR and ENDOR Study of a series of free base porphycenes in the photoexcited triplet state. Appl Magn Reson 1993, 4, 321. <http://dx.doi.org/10.1007/BF03162505>
  • Zhongying Hu, Scordilis-Kelley Chariclea, Cava Michael P.: New thiophene-derived 28-π annulenes. Tetrahetron Lett 1993, 34, 1879. <http://dx.doi.org/10.1016/S0040-4039(00)91952-X>
  • Lash Timothy D., Armiger Yoek Lin See-Tow: Conjugated macrocycles related to the porphyrins. Part 2. Further synthetic and spectroscopic studies on difuryl analogs of the oxophlorins. J Heterocyclic Chem 1991, 28, 965. <http://dx.doi.org/10.1002/jhet.5570280421>
  • Jux Norbert, Koch Peter, Schmickler Hans, Lex Johann, Vogel Emanuel: Acetylen-Cumulen-Porphyrinoide. Angew Chem 1990, 102, 1429. <http://dx.doi.org/10.1002/ange.19901021205>
  • Vogel Emanuel, Jux Norbert, Rodriguez-Val Eduardo, Lex Johann, Schmickler Hans: Die Porphyrin-Homologen: [22]Porphyrin (2.2.2.2), ein „gestrecktes Porphycen”. Angew Chem 1990, 102, 1431. <http://dx.doi.org/10.1002/ange.19901021206>
  • Will Stefan, Rahbar Afssaneh, Schmickler Hans, Lex Johann, Vogel Emanuel: Isocorrole: Neuartige tetrapyrrolische Makrocyclen. Angew Chem 1990, 102, 1434. <http://dx.doi.org/10.1002/ange.19901021207>