Pentacene

Pentacene
Skeletal formula of pentacene
Space-filling model of the pentacene molecule
Names
Preferred IUPAC name
Pentacene
Other names
2,3:6,7-Dibenzanthracene
Benzo[b]naphthacene
Dibenz[b,i]anthracene
NSC 90784
lin-Dibenzanthracene
lin-Naphthoanthracene
Identifiers
3D model (JSmol)
1912418
ChEBI
ChemSpider
ECHA InfoCard 100.004.722 Edit this at Wikidata
EC Number
  • 205-193-7
733903
UNII
  • InChI=1S/C22H14/c1-2-6-16-10-20-14-22-12-18-8-4-3-7-17(18)11-21(22)13-19(20)9-15(16)5-1/h1-14H checkY
    Key: SLIUAWYAILUBJU-UHFFFAOYSA-N checkY
  • InChI=1/C22H14/c1-2-6-16-10-20-14-22-12-18-8-4-3-7-17(18)11-21(22)13-19(20)9-15(16)5-1/h1-14H
    Key: SLIUAWYAILUBJU-UHFFFAOYAR
  • c1ccc2cc3cc4cc5ccccc5cc4cc3cc2c1
Properties
C22H14
Molar mass 278.354 g·mol−1
Appearance Dark blue powder
Density 1.3 g cm−3
Melting point > 300 °C (572 °F; 573 K) sublimes at 372 °C
Boiling point 40–43 °C (104–109 °F; 313–316 K) at 0.15 torr
-205.4 × 10−6 cm3 mol−1
Structure
Triclinic
P-1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Pentacene (C22H14) is a polycyclic aromatic hydrocarbon consisting of five linearly-fused benzene (C6H6) rings. This highly conjugated compound is an organic semiconductor. The compound generates excitons upon absorption of ultra-violet (UV) or visible light; this makes it very sensitive to oxidation. For this reason, this compound, which is a purple powder, slowly degrades upon exposure to air and light.

Structurally, pentacene is one of the linear acenes, the previous one being tetracene (four fused benzene rings) and the next one being hexacene (six fused benzene rings). In August 2009, a group of researchers from IBM published experimental results of imaging a single molecule of pentacene using an atomic force microscope.[1][2] In July 2011, they used a modification of scanning tunneling microscopy to experimentally determine the shapes of the highest occupied and lowest unoccupied molecular orbitals.[3][4]

In 2012, pentacene-doped p-terphenyl was shown to be effective as the amplifier medium for a room-temperature maser.[5]

  1. ^ "Single molecule's stunning image". BBC News. 2009-08-28. Retrieved 2009-08-28.
  2. ^ Gross, L.; Mohn, F; Moll, N; Liljeroth, P; Meyer, G (2009). "The Chemical Structure of a Molecule Resolved by Atomic Force Microscopy". Science. 325 (5944): 1110–1114. Bibcode:2009Sci...325.1110G. doi:10.1126/science.1176210. PMID 19713523. S2CID 9346745.
  3. ^ Krieger, K. (23 August 2011). "Molecules Imaged Most Intimately". Science Now. Retrieved 29 June 2017.
  4. ^ Gross, L.; Moll, N.; Mohn, F.; Curioni, A.; Meyer, G.; Hanke, F.; Persson, M. (2011). "High-Resolution Molecular Orbital Imaging Using a p-Wave STM Tip". Phys. Rev. Lett. 107 (8): 86101–86104. Bibcode:2011PhRvL.107h6101G. doi:10.1103/PhysRevLett.107.086101. PMID 21929180.
  5. ^ Brumfiel, G. (2012). "Microwave laser fulfills 60 years of promise". Nature. doi:10.1038/nature.2012.11199. S2CID 124247048.