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Pure Appl. Chem., 1980, Vol. 52, No. 6, pp. 1549-1563

http://dx.doi.org/10.1351/pac198052061549

Electronic structure of aromatic π-electron systems as reflected in their MCD spectra

J. Michl

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  • Gai Lizhi, Mack John, Lu Hua, Yamada Hiroko, Kuzuhara Daiki, Lai Guoqiao, Li Zhifang, Shen Zhen: New 2,6-Distyryl-Substituted BODIPY Isomers: Synthesis, Photophysical Properties, and Theoretical Calculations. Chem. Eur. J. 2014, 20, 1091. <http://dx.doi.org/10.1002/chem.201303291>
  • Mack John, Otaki Tatsuya, Durfee William S., Kobayashi Nagao, Stillman Martin J.: MCD spectroscopy and TD-DFT calculations of low symmetry subnaphthalocyanine analogs. Journal of Inorganic Biochemistry 2014. <http://dx.doi.org/10.1016/j.jinorgbio.2014.01.001>
  • Liang Xu, Mack John, Zheng Li-Min, Shen Zhen, Kobayashi Nagao: Phosphorus(V)-Corrole: Synthesis, Spectroscopic Properties, Theoretical Calculations, and Potential Utility for in Vivo Applications in Living Cells. Inorg. Chem. 2014, 53, 2797. <http://dx.doi.org/10.1021/ic402347w>
  • Okujima Tetsuo, Ando Chie, Mack John, Mori Shigeki, Hisaki Ichiro, Nakae Takahiro, Yamada Hiroko, Ohara Keishi, Kobayashi Nagao, Uno Hidemitsu: Acenaphthylene-Fused Cyclo[8]pyrroles with Intense Near-IR-Region Absorption Bands. Chem. Eur. J. 2013, 19, 13970. <http://dx.doi.org/10.1002/chem.201301294>
  • Mack John, Morita Yuki, Higashibayashi Shuhei, Sakurai Hidehiro, Kobayashi Nagao: Magnetic circular dichroism spectroscopy and electronic structures of C3 symmetry buckybowls. Chemical Physics Letters 2013, 556, 188. <http://dx.doi.org/10.1016/j.cplett.2012.11.042>
  • Sugawara Shun, Hirata Yusuke, Kojima Satoshi, Yamamoto Yohsuke, Miyazaki Eigo, Takimiya Kazuo, Matsukawa Shiro, Hashizume Daisuke, Mack John, Kobayashi Nagao: Synthesis, Characterization, and Spectroscopic Analysis of Antiaromatic Benzofused Metalloporphyrins. Chemistry A European Journal 2012, 18, 3566. <http://dx.doi.org/10.1002/chem.201101846>
  • Kon-no Masaru, Mack John, Kobayashi Nagao, Suenaga Masahiko, Yoza Kenji, Shinmyozu Teruo: Synthesis, Optical Properties, and Electronic Structures of Fully Core-Modified Porphyrin Dications and Isophlorins. Chem. Eur. J. 2012, 18, 13361. <http://dx.doi.org/10.1002/chem.201200776>
  • Xu Hai-Jun, Mack John, Wu Di, Xue Zhao-Li, Descalzo Ana B., Rurack Knut, Kobayashi Nagao, Shen Zhen: Synthesis and Properties of Fused-Ring-Expanded Porphyrins that were Core-Modified with Group 16 Heteroatoms. Chem. Eur. J. 2012, 18, 16844. <http://dx.doi.org/10.1002/chem.201200956>
  • Matsushita Osamu, Derkacheva Valentina M., Muranaka Atsuya, Shimizu Soji, Uchiyama Masanobu, Luk’yanets Evgeny A., Kobayashi Nagao: Rectangular-Shaped Expanded Phthalocyanines with Two Central Metal Atoms. S J Am Chem Soc 2012, 134, 3411. <http://dx.doi.org/10.1021/ja209589x>
  • Kobayashi Nagao, Asano Yoshiaki, Sato Jun, Furuyama Taniyuki: A zinc gable phthalocyanine and a derived planar bis-phthalocyanine containing a shared anthracene unit. Chem Commn 2012, 48, 4365. <http://dx.doi.org/10.1039/c2cc31264f>
  • Honda Tatsuhiko, Kojima Takahiko, Kobayashi Nagao, Fukuzumi Shunichi: Crystal Structures and Electronic Properties of Saddle-Distorted and Protonated Phthalocyanines. angew chemie 2011, 123, 2777. <http://dx.doi.org/10.1002/ange.201006607>
  • Okujima Tetsuo, Jin Guangnan, Matsumoto Naoki, Mack John, Mori Shigeki, Ohara Keishi, Kuzuhara Daiki, Ando Chie, Ono Noboru, Yamada Hiroko: Cyclo[8]isoindoles: Ring-Expanded and Annelated Porphyrinoids. angew chemie 2011, 123, 5817. <http://dx.doi.org/10.1002/ange.201007510>
  • Honda Tatsuhiko, Kojima Takahiko, Kobayashi Nagao, Fukuzumi Shunichi: Crystal Structures and Electronic Properties of Saddle-Distorted and Protonated Phthalocyanines. Angew Chem Int E 2011, 50, 2725. <http://dx.doi.org/10.1002/anie.201006607>
  • Okujima Tetsuo, Jin Guangnan, Matsumoto Naoki, Mack John, Mori Shigeki, Ohara Keishi, Kuzuhara Daiki, Ando Chie, Ono Noboru, Yamada Hiroko: Cyclo[8]isoindoles: Ring-Expanded and Annelated Porphyrinoids. Angew Chem Int E 2011, 50, 5699. <http://dx.doi.org/10.1002/anie.201007510>
  • Xue Zhao Li, Mack John, Lu Hua, Zhang Lei, You Xiao Zeng, Kuzuhara Daiki, Stillman Martin, Yamada Hiroko, Yamauchi Seigo, Kobayashi Nagao: The Synthesis and Properties of Free-Base [14]Triphyrin(2.1.1) Compounds and the Formation of Subporphyrinoid Metal Complexes. Chem Eur J 2011, 17, 4396. <http://dx.doi.org/10.1002/chem.201003100>
  • Tiedemann Michael T., Stillman Martin J.: Application of magnetic circular dichroism spectroscopy to porphyrins, phthalocyanines and hemes. J. Porphyrins Phthalocyanines 2011, 15, 1134. <http://dx.doi.org/10.1142/S1088424611004269>
  • 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>
  • Mack John, Bunya Masaru, Shimizu Yusuke, Uoyama Hiroki, Komobuchi Naoki, Okujima Tetsuo, Uno Hidemitsu, Ito Satoshi, Stillman Martin J., Ono Noboru: Application of MCD Spectroscopy and TD-DFT to Nonplanar Core-Modified Tetrabenzoporphyrins: Effect of Reduced Symmetry on Nonplanar Porphyrinoids. Chem Eur J 2008, 14, 5001. <http://dx.doi.org/10.1002/chem.200701611>
  • Mack John, Asano Yoshiaki, Kobayashi Nagao, Stillman Martin J.: Magnetic circular dichroism spectroscopy of cobalt tetraphenyltetraacenaphthoporphyrin. J  Inorg Biochem 2008, 102, 472. <http://dx.doi.org/10.1016/j.jinorgbio.2007.10.031>
  • Mack John, Stillman Martin J., Kobayashi Nagao: Application of MCD spectroscopy to porphyrinoids. Coord Chem Rev - 2007, 251, 429. <http://dx.doi.org/10.1016/j.ccr.2006.05.011>
  • Kobayashi Nagao, Nakai Katsunori: Applications of magnetic circular dichroism spectroscopy to porphyrins and phthalocyanines. Chem Commun 2007, 4077. <http://dx.doi.org/10.1039/b704991a>
  • MACK JOHN, STILLMAN MARTIN J.: Assignment of the optical spectrum of metal porphyrin and phthalocyanine radical anions. J. Porphyrins Phthalocyanines 2001, 05, 67. <http://dx.doi.org/10.1002/1099-1409(200101)5:1<67::AID-JPP300>3.0.CO;2-3>
  • Mack John, Stillman Martin J.: Assignment of the optical spectrum of metal porphyrin and phthalocyanine radical anions. J Porphyrins Phthalocyanines 2001, 5, 67. <http://dx.doi.org/10.1002/1099-1409(200101)5:1<67::AID-JPP300>3.0.CO;2-3>
  • Barnes N. Randy, Stroud Peter D., Robinson Katie E., Horton Carl, Schreiner Anton F.: 5,10,15,20-Tetrakis(4-N-methylpyridyl)porphyrinatopalladium(II) as a differentiation probe for sensing binding modes with B-DNA duplexes: Electronic MCD and CD spectra. Biospectroscopy 1999, 5, 179. <http://dx.doi.org/10.1002/(SICI)1520-6343(1999)5:3<179::AID-BSPY7>3.0.CO;2-U>
  • Barnes N. Randy, Schreiner Anton F., Finnegan Michael G., Johnson Michael K.: Insight into externally bound 5,10,15,20-tetrakis(2-N-methylpyridyl)porphyrinatopalladium(II), PdP(2), with B-form DNA duplexes poly(G-C)2, poly(A-T)2, and CT DNA by using combined MCD, CD, and optical data. Biospectroscopy 1998, 4, 341. <http://dx.doi.org/10.1002/(SICI)1520-6343(1998)4:5<341::AID-BSPY5>3.0.CO;2-E>
  • Randy Barnes N., Schreiner Anton F., Dolan Michael A.: Measurement and interpretation of Q0 and Q1 band property changes of two cationic metalloporphyrins upon binding with B-DNA: electronic MCD, CD, and optical absorption. J  Inorg Biochem 1998, 72, 1. <http://dx.doi.org/10.1016/S0162-0134(98)10050-8>
  • Goldbeck Robert A., Kim-Shapiro Daniel B., Kliger David S.: FAST NATURAL AND MAGNETIC CIRCULAR DICHROISM SPECTROSCOPY. Ann Rev Phys Chem 1997, 48, 453. <http://dx.doi.org/10.1146/annurev.physchem.48.1.453>
  • Isago Hiroaki, Kagaya Yutaka: Spectroscopic Properties of One-Electron-Reduced Species of Dichloro(phthalocyaninato)antimony(V) Cation. Bull Chem Soc Jpn 1996, 69, 1281. <http://dx.doi.org/10.1246/bcsj.69.1281>
  • Yoshimura Tetsuhiko, Toi Hiroo, Inaba Shinji, Ogoshi Hisanobu: Bis(1-methylimidazole)iron(II) Complexes of Porphyrins Substituted with Highly Electron-Withdrawing CF3 Groups: Electronic Spectra with Split Q-Bands and MCD Spectra with Unusual Features. Bull Chem Soc Jpn 1992, 65, 1915. <http://dx.doi.org/10.1246/bcsj.65.1915>
  • Keegan Joseph D., Bunnenberg Edward, Djerassi Carl: Magnetic circular dichroism studies���63. Sign variation in the magnetic circular dichroism spectra of some perimeter symmetric metallo porphyrins. Spectrochimica Acta Part A: Molecular Spectroscopy 1984, 40, 287. <http://dx.doi.org/10.1016/0584-8539(84)80051-3>
  • Lu Yucheng, Shu Arthur Y.L., Knierzinger Andreas, Clezy Peter S., Bunneberg Edward, Djerassi Carl: Novel magnetic circular dichroism spectra of monoacetyl porphyrins. Structure implications. Tetrahetron Lett 1983, 24, 2433. <http://dx.doi.org/10.1016/S0040-4039(00)81947-4>
  • Keegan Joseph D., Bunnenberg Edward, Djerassi Carl: Magnetic Circular Dichroism Studies. 62.1 Sign Variation in the Magnetic Circular Dichroism Spectra of Some Perimeter Symmetric Free-Base Porphyrins. Spec Lett 1983, 16, 275. <http://dx.doi.org/10.1080/00387018308062345>