Chemistry:Pentaphene
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, characterized by a central naphthalene unit with additional benzene rings fused in a nonlinear, angular pattern. Its chemical formula is C
22H
14.[1]
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.
The distinction between acenes and phenes is based on ring topology. Acenes are composed of linearly fused benzene rings (e.g., naphthalene, anthracene, tetracene, pentacene). Phenes, such as phenanthrene, chrysene, and picene, feature a bend in their structure due to angular fusions. Pentaphene is considered to be one of the largest stable phenes.
Synthesis
The compound can be prepared from o-benzylbenzoic acid in a six-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
- ↑ "Pentaphene" (in en). NIST. https://webbook.nist.gov/cgi/cbook.cgi?ID=C222935&Units=SI.
- ↑ Franck, Heinz‐Gerhard; Zander, Maximilian (February 1966). "Eine neue Synthese des Pentaphens". Chemische Berichte 99 (2): 396–398. doi:10.1002/cber.19660990205. https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cber.19660990205. Retrieved 31 March 2026.
- ↑ CRC Handbook of Chemistry and Physics: A Ready-Reference Book of Chemical and Physical Вata (87, 2006-2007 ed.). Boca Raton, Fla.: CRC, Taylor & Francis. 2006. p. 454. ISBN 978-0-8493-0487-3. https://ia601308.us.archive.org/27/items/CRC.Press.Handbook.of.Chemistry.and.Physics.85th.ed.eBook-LRN/CRC.Press.Handbook.of.Chemistry.and.Physics.85th.ed.eBook-LRN.pdf. Retrieved 31 March 2026.
- ↑ Dictionary of Organic Compounds (6. ed.). London Weinheim: Chapman and Hall. 1996. p. 5125. ISBN 0-412-54090-8. https://www.google.nl/books/edition/Dictionary_of_Organic_Compounds_Sixth_Ed/xfsR6iJ1HGgC?hl=en&gbpv=1&dq=Dictionary+of+organic+compounds+(6.+ed.)&pg=PP2&printsec=frontcover. Retrieved 31 March 2026.
 |  |
