''N''-Vinylcarbazole

N-vinylcarbazole[1]
Names
IUPAC name
9-ethenyl-9H-carbazole
Other names
9-vinyl-9H-carbazole, NVC
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.596
EC Number 216-055-0
RTECS number FE6350000
Properties
C14H11N
Molar mass 193.244 g mol−1
Appearance pale brown crystalline solid[2]
Melting point 66 °C (151 °F; 339 K)
Boiling point 154 to 155 °C (309 to 311 °F; 427 to 428 K) 3 mmHg[2]
insoluble
Solubility in diethyl ether very soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

N-Vinylcarbazole is an organic compound used as a monomer in the production of poly(vinylcarbazole),[3] a conductive polymer, in which conductivity is photon-dependent. The compound is used in the photoreceptors of photocopiers.[4] Upon exposure to γ-irradiation, N-vinylcarbazole undergoes solid-state polymerisation.[5]

Synthesis

One possible synthesis, patented by Nippon Shokubai, is based on the reaction of carbazole with ethylene carbonate at 300 °C (572 °F)-500 °C (932 °F) under partial vacuum and in the presence of alkaline earth metal and alkaline metal catalyst and silica. This reaction produces N-(2-Hydroxyethyl) carbazole, which in turn generates vinylcarbazole through water eliminiation.[3]

References

  1. ↑ Lide, David R. (2008). CRC Handbook of Chemistry and Physics, 89th Edition. CRC Press. pp. 3–518. ISBN 978-0-8493-0488-0.
  2. 1 2 Sigma-Aldrich 9-Vinylcarbazole product page
  3. 1 2 Conti, Francsco (June 2006). "Nuova via di sintesi del vinilcarbazolo". La Chimica & L'Industria (in Italian). Società Chimica Italiana (5): 82.
  4. ↑ G. Burton; J. Holman; J. Lazonby; G. Pilling; D. Waddington (2000). Chemical Storylines (2nd ed.). Heinemann Educational Publishers. pp. 121–122. ISBN 0-435-63119-5.
  5. ↑ K. Tsutsui; K. Hirotsu; M. Umesaki; M. Kurahashi; A. Shimada; T. Higuchi (1976). "Structural chemistry of polymerizable monomers. I. Crystal structure of N-vinylcarbazole". Acta Crystallogr. B. 32: 3049–3053. doi:10.1107/S0567740876009527.
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