Tetraphenylmethane

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Structural formula
Structural formula of tetraphenylmethane
General
Surname Tetraphenylmethane
other names

1,1,1,1-methanetetrayl tetrakisbenzene

Molecular formula C 25 H 20
Brief description
  • white to pink solid
  • colorless crystals
External identifiers / databases
CAS number 630-76-2
EC number 211-144-0
ECHA InfoCard 100.010.132
PubChem 12424
Wikidata Q420710
properties
Molar mass 320.42 g mol −1
Physical state

firmly

density

1.217 g cm −1

Melting point

281-286 ° C , 285 ° C

boiling point

431 ° C

solubility
safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tetraphenylmethane was first synthesized in 1896/1897 by the chemist Moses Gomberg together with Adolf von Baeyer , Johannes Thiele and Victor Meyer . Compounds derived from tetraphenylmethane are now used as material for OLEDs .

Structurally similar compounds are e.g. B. triphenyl methane and sodium tetraphenyl borate .

Presentation and extraction

The synthesis of tetraphenylmethane takes place in a three-stage synthesis. The first step is a Friedel-Crafts alkylation of anilinium chloride with triphenylmethanol . The intermediate product is then diazotized . The target compound then results from a reduction with phosphinic acid .

properties

Tetraphenylmethane forms colorless crystals that melt at 285 ° C with a heat of fusion of 48.28 kJ mol −1 . The connection tends at temperatures from 90 ° C to sublimation . The vapor pressure function results according to August according to ln (P) = A + B / T ( P in Pa, T in K) with A = 38.02 and B = −16280 in the temperature range from 90 ° C to 115 ° C. The heat of sublimation is 135.4 kJ mol −1 . The connection is in a tetragonal crystal lattice.

Web links

Commons : Tetraphenylmethane  - Collection of Images, Videos, and Audio Files

literature

  • M. Gomberg, Oliver Kamm: Tetraphenylmethane , in: J. Am. Chem. Soc. , 1917 , 39  (9), pp. 2009-2015 ( doi: 10.1021 / ja02254a016 ).
  • Hsiu-Chih Yeh, Rong-Ho Lee, Li-Hsin Chan, Tzu-Yao Jeremy Lin, Chin-Ti Chen, Easwaramoorthy Balasubramaniam, Yu-Tai Tao: Synthesis, Properties, and Applications of Tetraphenylmethane-Based Molecular Materials for Light-Emitting Devices , in: Chem. Mater. , 2001 , 13  (9), pp. 2788-2796 ( doi: 10.1021 / cm0008056 ).
  • Kacey Claborn, Bart Kahra, Werner Kaminsky: Calculations of optical properties of the tetraphenyl-X family of isomorphous crystals (X = C, Si, Ge, Sn, Pb) . In: CrystEngComm . tape 4 , no. 46 , 2002, doi : 10.1039 / B202304K ( PDF ).

Individual evidence

  1. ↑ a b c d data sheet tetraphenylmethane from Acros, accessed on February 19, 2010.
  2. ↑ a b c d e f g Entry on tetraphenylmethane. In: Römpp Online . Georg Thieme Verlag, accessed on November 01, 2016.
  3. ↑ a b Data sheet Tetraphenylmethane, 96% from AlfaAesar, accessed on November 1, 2016 ( PDF )(JavaScript required) .
  4. ↑ Patent US7052783 : Oxadiazole tetramers. Published on August 1, 2002 , Inventors: LEE RONG-HO, CHEN CHIN-TI, YEH HSIU-CHIH, CHAN LI-HSIN. ‌
  5. ↑ a b c d Verevkin, SP: Thermochemical Properties of Triphenylalkanes and Tetraphenylmethane. Strain in Phenyl Substituted Alkanes in J. Chem. Eng. Data 44 (1999) 557-562, doi: 10.1021 / je9802726 .
  6. ↑ Osvald Knop, Kathryn N. Rankin, T. Stanley Cameron, Russell J. Boyd: Crystal chemistry of tetraradial species. Part 10. Tilting at windmills: conformations of the tetraphenyl species ZPh 4 0, ± 1 (Z = B, C, N) . In: Canadian Journal of Chemistry . tape 80 , no. 10 , 2002, p. 1351-1366 , doi : 10.1139 / v02-171 .