Pentaphene

Pentaphene
Names
Preferred IUPAC name
Pentaphene
Other names
  • Dibenzo[b,h]phenanthrene
  • 2,3:6,7-Dibenzphenanthrene
Identifiers
3D model (JSmol)
2051200
ChEBI
ChemSpider
ECHA InfoCard 100.005.389
EC Number
  • 205-927-6
UNII
  • InChI=1S/C22H14/c1-3-7-17-13-21-19(11-15(17)5-1)9-10-20-12-16-6-2-4-8-18(16)14-22(20)21/h1-14H
    Key: JQQSUOJIMKJQHS-UHFFFAOYSA-N
  • C=1C=CC=2C=C3C(C=CC=4C=C5C=CC=CC5=CC43)=CC2C1
Properties
C22H14
Molar mass 278.354 g·mol−1
Appearance greenish-yellow solid
Density 1.2 g/cm3
Melting point 275 °C (527 °F; 548 K)
Boiling point 524 °C (975 °F; 797 K)
insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Pentaphene is a polycyclic aromatic hydrocarbon consisting of five linearly fused benzene rings. The compound is a structural isomer of the more common pentacene, from which it differs by the arrangement of its rings. While pentacene has a linear acene structure, pentaphene is a peri-fused compound, with an angular fusion along the five-ring structure. Its chemical formula is C22H14.

Structure

Pentaphene structure can be visualized as a naphthalene core with additional benzene rings fused in a V-shape manner. This angular geometry contrasts with the fully linear, rod-like shape of its isomer, pentacene.

Synthesis

The compound can be prepared from o-benzylbenzoic acid in a six-step synthesis.[1]

Also, pentaphene can be prepared via 1,2-anthracyne, through a multi-step synthesis.[2]

Physical properties

The greenish-yellow compound is insoluble in water or ethanol, but soluble in nonpolar organic solvents, such as xylene and diethyl ether.[3] Under UV light, penthaphene exhibits intense blue fluorescence.[4]

Uses

This compound is of significant interest in the fields of organic electronics, materials science, and theoretical chemistry due to its unique electronic structure and photophysical properties.

References

  1. ^ Franck, Heinz-Gerhard; Zander, Maximilian (February 1966). "Eine neue Synthese des Pentaphens". Chemische Berichte. 99 (2): 396–398. doi:10.1002/cber.19660990205.
  2. ^ Camenzind, Robert; Rickborn, Bruce (May 1986). "Pentaphene via 1,2-anthracyne: an application of repeated aryne–isobenzofuran methodology". The Journal of Organic Chemistry. 51 (10): 1914–1916. doi:10.1021/jo00360a054.
  3. ^ CRC Handbook of Chemistry and Physics: A Ready-Reference Book of Chemical and Physical Вata (PDF) (87, 2006-2007 ed.). Boca Raton, Fla.: CRC, Taylor & Francis. 2006. p. 454. ISBN 978-0-8493-0487-3. Retrieved 31 March 2026.
  4. ^ Dictionary of Organic Compounds (6. ed.). London Weinheim: Chapman and Hall. 1996. p. 5125. ISBN 0-412-54090-8. Retrieved 31 March 2026.
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