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Synthesis, π‐Face‐Selective Aggregation,and π‐Face Chiral Recognition of Configurationally Stable C3‐Symmetric Propeller‐Chiral Molecules with a π‐Core
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Dr. Nozomi Saito Dr. Ryo Terakawa Prof. Dr. Masahiko Yamaguchi 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(19):5601-5607
The C3‐symmetric propeller‐chiral compounds (P,P,P)‐ 1 and (M,M,M)‐ 1 with planar π‐cores perpendicular to the C3‐axis were synthesized in optically pure states. (P,P,P)‐ 1 possesses two distinguishable propeller‐chiral π‐faces with rims of different heights named the (P/L)‐face and (P/H)‐face. Each face is configurationally stable because of the rigid structure of the helicenes contained in the π‐core. (P,P,P)‐ 1 formed dimeric aggregates in organic solutions as indicated by the results of 1H NMR, CD, and UV/Vis spectroscopy and vapor pressure osmometry analyses. The (P/L)/(P/L) interactions were observed in the solid state by single‐crystal X‐ray analysis, and they were also predominant over the (P/H)/(P/H) and (P/L)/(P/H) interactions in solution, as indicated by the results of 1H and 2D NMR spectroscopy analyses. The dimerization constant was obtained for a racemic mixture, which showed that the heterochiral (P,P,P)‐ 1 /(M,M,M)‐ 1 interactions were much weaker than the homochiral (P,P,P)‐ 1 /(P,P,P)‐ 1 interactions. The results indicated that the propeller‐chiral (P/L)‐face interacts with the (P/L)‐face more strongly than with the (P/H)‐face, (M/L)‐face, and (M/H)‐face. The study showed the π‐face‐selective aggregation and π‐face chiral recognition of the configurationally stable propeller‐chiral molecules. 相似文献
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Back Cover: Synthesis, π‐Face‐Selective Aggregation,and π‐Face Chiral Recognition of Configurationally Stable C3‐Symmetric Propeller‐Chiral Molecules with a π‐Core (Chem. Eur. J. 19/2014)
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Dr. Nozomi Saito Dr. Ryo Terakawa Prof. Dr. Masahiko Yamaguchi 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(19):5844-5844
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T. Narasimhamurthy J. C. N. Benny K. Pandiarajan Ravindranath S. Rathore 《Acta Crystallographica. Section C, Structural Chemistry》2003,59(11):o620-o621
The structure of the title compound, C17H16OS, is primarily stabilized by T‐shaped and parallel‐displaced aromatic clusters. The distances between the centroids of the aromatic pairs are in the range 4.34–5.30 Å. In the crystal packing, the molecules dimerize by means of π–π interactions of both face‐to‐face and edge‐to‐face types, and the aromatic rings associate in a cyclic edge‐to‐face tetrameric arrangement of the herring‐bone type. These herring‐bone interactions appear to insulate hydrogen‐bond interactions in the crystal structure. 相似文献
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Ligia R. Gomes John Nicolson Low James L. Wardell Laura N. de F. Cardoso Marcus V. N. De Souza 《Acta Crystallographica. Section C, Structural Chemistry》2013,69(2):191-194
The molecules of 4‐allyloxy‐7‐chloroquinoline, C12H10ClNO, (I), 7‐chloro‐4‐methoxyquinoline, C10H8ClNO, (II), and 7‐chloro‐4‐ethoxyquinoline, C11H10ClNO, (III), are all planar. In all three structures, π–π interactions between the quinoline ring systems are generated by unit‐cell translations along the a axes, irrespective of space group. These structures are the first reported for 4‐alkoxyquinolines. 相似文献
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Redox‐Switchable 20π‐, 19π‐, and 18π‐Electron 5,10,15,20‐Tetraaryl‐5,15‐diazaporphyrinoid Nickel(II) Complexes
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Takaharu Satoh Prof. Dr. Mao Minoura Prof. Dr. Haruyuki Nakano Prof. Dr. Ko Furukawa Prof. Dr. Yoshihiro Matano 《Angewandte Chemie (International ed. in English)》2016,55(6):2235-2238
The first examples of air‐stable 20π‐electron 5,10,15,20‐tetraaryl‐5,15‐diaza‐5,15‐dihydroporphyrins, their 18π‐electron dications, and the 19π‐electron radical cation were prepared through metal‐templated annulation of nickel(II) bis(5‐arylamino‐3‐chloro‐8‐mesityldipyrrin) complexes followed by oxidation. The neutral 20π‐electron derivatives are antiaromatic and the cationic 18π‐electron derivatives are aromatic in terms of the magnetic criterion of aromaticity. The meso N atoms in these diazaporphyrinoids give rise to characteristic redox and optical properties for the compounds that are not typical of isoelectronic 5,10,15,20‐tetraarylporphyrins. 相似文献