Triphenylene
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | Triphenylene | |||||||||||||||
other names |
9,10-benzophenanthrene |
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Molecular formula | C 18 H 12 | |||||||||||||||
Brief description |
white to light yellow solid |
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properties | ||||||||||||||||
Molar mass | 228.29 g mol −1 | |||||||||||||||
Physical state |
firmly |
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density |
1.12 g cm −3 |
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Melting point |
195-198 ° C |
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boiling point |
438 ° C |
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solubility |
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safety instructions | ||||||||||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Triphenylene is a chemical compound from the group of polycyclic aromatic hydrocarbons and consists of four linked rings.
Occurrence
Triphenylene occurs naturally in coal tar and fossil fuels.
Extraction and presentation
Triphenylene can be obtained by a modified Haworth reaction starting from succinic anhydride with 9-phenanthrylmagnesium bromide and subsequent cyclization with hydrogen fluoride . Other synthetic methods are also known. The most common synthesis starts from cyclohexanone .
properties
Triphenylene is a white to light yellow solid that is insoluble in water. It has an orthorhombic crystal structure with the space group P 2 1 2 1 2 1 (space group no. 19) .
use
Triphenylene derivatives are used as liquid crystals.
Individual evidence
- ↑ a b c d e data sheet triphenylene, 98% from Sigma-Aldrich , accessed on October 18, 2015 ( PDF ).
- ^ Carl L. Yaws: Thermophysical Properties of Chemicals and Hydrocarbons . William Andrew, 2014, ISBN 978-0-323-29060-9 , pp. 335 ( limited preview in Google Book search).
- ↑ a b c d William M. Haynes: CRC Handbook of Chemistry and Physics, 96th Edition . CRC Press, 2015, ISBN 978-1-4822-6097-7 , pp. 540 ( limited preview in Google Book search).
- ↑ a b Entry on triphenylene in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
- ^ A b Ronald G. Harvey: Polycyclic Aromatic Hydrocarbons Chemistry and Carcinogenicity . CUP Archive, 1991, ISBN 978-0-521-36458-4 , pp. 157 ( limited preview in Google Book search).
- ↑ Eric Clar: Polycyclic Hydrocarbons . Springer Science & Business Media, 2013, ISBN 978-3-662-01665-7 , pp. 241 ( limited preview in Google Book search).
- ↑ FR Ahmed, J. Trotter: The crystal structure of triphenylene. In: Acta Crystallographica. 16, 1963, p. 503, doi : 10.1107 / S0365110X63001365 .
- ^ Glenn H. Brown: Advances in Liquid Crystals . Academic Press, 2013, ISBN 978-1-4831-9137-9 , pp. 47 ( limited preview in Google Book search).