Hexabenzocoronen
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Surname | Hexabenzocoronen | ||||||||||||
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Molecular formula | C 42 H 18 | ||||||||||||
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Molar mass | 522.59 g mol −1 | ||||||||||||
Physical state |
firmly |
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Melting point |
954 ° C |
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Hexabenzocoronen (more precisely hexa-peri-hexabenzocoronen) is a chemical compound from the group of polycyclic aromatic hydrocarbons . It consists of a coronene ring with a ring of benzene rings . Due to the special, highly symmetrical molecular structure, the connection is extremely stable.
Extraction and presentation
Some synthetic routes have been described for the synthesis of hexabenzocorones since the early 20th century. In 1958 , Erich Clar developed a synthesis route for hexabenzocorones starting from 2: 3-7: 8-dibenzo-peri-naphthalene as the first method of preparation, in which the starting compound is first converted to tetrabenzoperopyrene by bromination and subsequent heating to 153 ° C , and then further Heating to 481 ° C results in the cyclodehydrogenation to hexabenzocoronen.
In another synthesis variant by W. Schmidt, a quinone derivative is reacted with phenyllithium and the intermediate product is first cyclized with a melt of aluminum trichloride and sodium chloride and then aromatized with copper at 400 ° C.
properties
Hexabenzocoronen is a solid with a monoclinic crystal structure with the space group P 2 1 / a (space group no. 14, position 3) .
Its structure was made visible with an atomic force microscope .
use
Compounds based on hexabenzocorones are used to improve solar cells .
Individual evidence
- ↑ Dongping Chen, Jethro Akroyd et al. a .: Solid-liquid transitions in homogenous ovalene, hexabenzocoronene and circumcoronene clusters: A molecular dynamics study. In: Combustion and Flame. 162, 2015, p. 486, doi : 10.1016 / j.combustflame.2014.07.025 .
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ Dieter A. Schlueter, Craig Hawker, Junji Sakamoto: Synthesis of Polymers New Structures and Methods . John Wiley & Sons, 2012, ISBN 3-527-64408-3 , pp. 377 ( limited preview in Google Book search).
- ^ Sandeep Kumar: Chemistry of Discotic Liquid Crystals From Monomers to Polymers . CRC Press, 2016, ISBN 978-1-4398-1145-0 , pp. 168 ( limited preview in Google Book search).
- ^ W. Hendel, ZH Khan, W. Schmidt: Hexa-peri-benzocoronene, a candidate for the origin of the diffuse interstellar visible absorption bands? In: Tetrahedron . 42, 1986, p. 1127, doi : 10.1016 / S0040-4020 (01) 87517-7 .
- ↑ Richard Goddard, Matthias W. Haenel u. a .: Crystallization of Large Planar Polycyclic Aromatic Hydrocarbons: The Molecular and Crystal Structures of Hexabenzo [bc, ef, hi, kl, no, qr] coronene and Benzo [1,2,3-bc: 4,5,6-b 'c'] dicoronene. In: Journal of the American Chemical Society . 117, 1995, p. 30, doi : 10.1021 / ja00106a004 .
- ↑ L. Gross, F. Mohn et al. a .: Bond-Order Discrimination by Atomic Force Microscopy. In: Science . 337, 2012, p. 1326, doi : 10.1126 / science.1225621 .
- ↑ Henk H. Dam, Kuan Sun et al. a .: Morphology Change and Improved Efficiency in Organic Photovoltaics via Hexa-para-hexabenzocoronene Templates. In: ACS Applied Materials & Interfaces . 6, 2014, p. 8824, doi : 10.1021 / am5015666 .