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Chen MK, Hsin HJ, Wu TC, et al. Highly curved bowl-shaped fragments of fullerenes: synthesis, structural analysis, and physical properties. Chemistry. 2013;20(2):598-608doi: 10.1002/chem.201303357.
Chen, M. K., Hsin, H. J., Wu, T. C., Kang, B. Y., Lee, Y. W., Kuo, M. Y., & Wu, Y. T. (2014). Highly curved bowl-shaped fragments of fullerenes: synthesis, structural analysis, and physical properties. Chemistry (Weinheim an der Bergstrasse, Germany), 20(2), 598-608. https://doi.org/10.1002/chem.201303357
Chen, Min-Kuan, et al. "Highly curved bowl-shaped fragments of fullerenes: synthesis, structural analysis, and physical properties." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 20,2 (2014): 598-608. doi: https://doi.org/10.1002/chem.201303357
Chen MK, Hsin HJ, Wu TC, Kang BY, Lee YW, Kuo MY, Wu YT. Highly curved bowl-shaped fragments of fullerenes: synthesis, structural analysis, and physical properties. Chemistry. 2014 Jan 07;20(2):598-608. doi: 10.1002/chem.201303357. Epub 2013 Dec 05. PMID: 24311153.
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Chemistry. 2014 Jan 07;20(2):598-608. doi: 10.1002/chem.201303357. Epub 2013 Dec 05.

Highly curved bowl-shaped fragments of fullerenes: synthesis, structural analysis, and physical properties.

Chemistry (Weinheim an der Bergstrasse, Germany)

Min-Kuan Chen, Hsin-Ju Hsin, Tsun-Cheng Wu, Bo-Yan Kang, Yen-Wei Lee, Ming-Yu Kuo, Yao-Ting Wu

Affiliations

  1. Department of Chemistry, National Cheng Kung University, No. 1 Ta-Hsueh Rd., 70101 Tainan (Taiwan).

PMID: 24311153 DOI: 10.1002/chem.201303357

Abstract

Highly curved buckybowls 3, 4, and 5 were synthesized from planar precursors, fluoranthenes 8, benzo[k]fluoranthenes 10 and naphtho[1,2-k]-cyclopenta[cd]fluoranthenes 12, respectively, using straightforward palladium-catalyzed cyclization reactions. These fluoranthene-based starting materials were easily prepared from 1,8-bis(arylethynyl)naphthalenes 6. Both buckybowls 3 and 4 are fragments of C60 , whereas 5 is a unique subunit of C70 . The curved structures were identified by X-ray crystallography, and they are deep bowls. The maximum π-orbital axis vector (POAV) pyramidalization angle in both 3 and 4 is 12.8°. Such a high curvature is very rarely obtained. Buckybowls 5 are less curved than the others because they have a lower density of five-membered rings, analogous to the tube portion of C70 . Cyclopentaannulation increases the bowl depths of 3 and 4, but not the maximum POAV pyramidalization angle. Among the eight buckybowls studied herein, five form polar crystals. The bowl-to-bowl inversion dynamics of these buckybowls can be classified into two types; one has a planar transition structure, whereas the other has an S-shaped transition structure. A larger longitudinal length of these buckybowls corresponds to a stronger preference for the latter. The photophysical properties of these buckybowls were examined and compared with those of C60 and C70 . Buckybowls 5 have absorption bands at wavelengths greater than 450 nm, which are similar to those of C70 . The chiral resolution of the mono-substituted buckybowl 4 ac was also studied by using HPLC with a chiral column.

Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: X-ray diffraction; fluoranthene; fullerene; palladium; rhodium

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