Chemistry:N-Vinylcarbazole

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N-vinylcarbazole[1]
N-vinylcarbazole-2D-skeletal.png
N-vinylcarbazole-from-xtal-3D-balls.png
Names
Preferred IUPAC name
9-Ethenyl-9H-carbazole
Other names
9-Vinyl-9H-carbazole, NVC
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 216-055-0
RTECS number
  • FE6350000
UNII
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]

It is produced by the vinylation of carbazole with acetylene in the presence of base.[6]

Related compounds

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. 2.0 2.1 Sigma-Aldrich 9-Vinylcarbazole product page
  3. Conti, Francsco (June 2006). "Nuova via di sintesi del vinilcarbazolo" (in it). La Chimica & L'Industria (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. https://archive.org/details/chemicalstorylin0000unse/page/121. 
  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. 
  6. Pässler, Peter; Hefner, Werner; Buckl, Klaus; Meinass, Helmut; Meiswinkel, Andreas; Wernicke, Hans-Jürgen; Ebersberg, Günter; Müller, Richard et al. (2008). "Acetylene Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_097.pub3. ISBN 3527306730.