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The Chiro-optical Properties of a Lemniscular Octaphyrin

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Department of Chemistry, Imperial College London, South Kensington Campus, Exhibition Road, London SW7 2AZ, U.K.
[email protected]
Cite this: Org. Lett. 2009, XXXX, XXX, XXX-XXX
Publication Date (Web):June 22, 2009
https://doi.org/10.1021/ol901172g
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Abstract

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The match between the calculated TD-DFT electronic circular dichroism spectrum of the M,M configuration of the lemniscular [36]octaphyrin 1 and the previously reported measured spectrum suggests that the assignment of the latter to the P,P enantiomer requires inverting to M,M. The unusually large magnitude of the calculated optical rotations for these species may reflect the aromatic character of the system.

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Cited By

This article is cited by 21 publications.

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  2. Takayuki Tanaka and Atsuhiro Osuka . Chemistry of meso-Aryl-Substituted Expanded Porphyrins: Aromaticity and Molecular Twist. Chemical Reviews 2017, 117 (4) , 2584-2640. https://doi.org/10.1021/acs.chemrev.6b00371
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  12. JUN-ICHIRO SETSUNE. Helical chirality induction of expanded porphyrin analogues. Journal of Chemical Sciences 2012, 124 (6) , 1151-1163. https://doi.org/10.1007/s12039-012-0315-4
  13. Shuang-Xi Gu, Zhi-Ming Li, Xiao-Dong Ma, Shi-Qiong Yang, Qiu-Qin He, Fen-Er Chen, Erik De Clercq, Jan Balzarini, Christophe Pannecouque. Chiral resolution, absolute configuration assignment and biological activity of racemic diarylpyrimidine CH(OH)-DAPY as potent nonnucleoside HIV-1 reverse transcriptase inhibitors. European Journal of Medicinal Chemistry 2012, 53 , 229-234. https://doi.org/10.1016/j.ejmech.2012.04.004
  14. Shohei Saito, Atsuhiro Osuka. Expandierte Porphyrine: überraschende Strukturen, elektronische Eigenschaften und Reaktivitäten. Angewandte Chemie 2011, 123 (19) , 4432-4464. https://doi.org/10.1002/ange.201003909
  15. Shohei Saito, Atsuhiro Osuka. Expanded Porphyrins: Intriguing Structures, Electronic Properties, and Reactivities. Angewandte Chemie International Edition 2011, 50 (19) , 4342-4373. https://doi.org/10.1002/anie.201003909
  16. Jun-ichiro Setsune, Miku Kawama, Takeshi Nishinaka. Helical binuclear CoII complexes of pyriporphyrin analogue for sensing homochiral carboxylic acids. Tetrahedron Letters 2011, 52 (15) , 1773-1777. https://doi.org/10.1016/j.tetlet.2011.02.013
  17. Kazuto Takaishi, Masuki Kawamoto. Synthesis and Conformation of Substituted Chiral Binaphthyl-Azobenzene Cyclic Dyads with Chiroptical Switching Capabilities. Molecules 2011, 16 (2) , 1603-1624. https://doi.org/10.3390/molecules16021603
  18. Takayuki Tanaka, Tsutomu Sugita, Sumito Tokuji, Shohei Saito, Atsuhiro Osuka. Metal Complexes of Chiral Möbius Aromatic [28]Hexaphyrin(1.1.1.1.1.1): Enantiomeric Separation, Absolute Stereochemistry, and Asymmetric Synthesis. Angewandte Chemie 2010, 122 (37) , 6769-6771. https://doi.org/10.1002/ange.201002282
  19. Takayuki Tanaka, Tsutomu Sugita, Sumito Tokuji, Shohei Saito, Atsuhiro Osuka. Metal Complexes of Chiral Möbius Aromatic [28]Hexaphyrin(1.1.1.1.1.1): Enantiomeric Separation, Absolute Stereochemistry, and Asymmetric Synthesis. Angewandte Chemie International Edition 2010, 49 (37) , 6619-6621. https://doi.org/10.1002/anie.201002282
  20. Pablo Rivera-Fuentes, José Lorenzo Alonso-Gómez, Ana G. Petrovic, Paul Seiler, Fabrizio Santoro, Nobuyuki Harada, Nina Berova, Henry S. Rzepa, François Diederich. Enantiomerically Pure Alleno-Acetylenic Macrocycles: Synthesis, Solid-State Structures, Chiroptical Properties, and Electron Localization Function Analysis. Chemistry - A European Journal 2010, 16 (32) , 9796-9807. https://doi.org/10.1002/chem.201001087
  21. Steven M. Bachrach. Computational organic chemistry. Annual Reports Section "B" (Organic Chemistry) 2010, 106 , 407. https://doi.org/10.1039/b927078g

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