Phosphaphenalene

Some isomeric phosphaphenalenes

1H-2-phosphaphenalene
CAS RN: 87954-77-6

Phosphaphenalenes are a class of heterocyclic aromatic compounds containing phosphorus with molecular formula C
₁₂H
₉P, related to the phenalene polycyclic aromatic hydrocarbons, C
₁₃H
₁₀.^[1] Phosphaphenalene can exist in a number of isomers depending on where in the ring system the phosphorus atom is placed. The phosphorus atom in these molecules has unusual properties, in particular changing its affinity as an electron acceptor when exposed to certain wavelengths of light. This makes phosphaphenalenes useful in optoelectronic applications such as temperature-dependent luminescence and electrochromism (reversibly changes colour when electricity is applied).^[2]^[3]

References[]

^ Trujillo, Cristina; Sánchez-Sanz, Goar; Alkorta, Ibon; Elguero, José (2017). "An insight on the aromatic changes in closed shell icosagen, tetrel, and pnictogen phenalenyl derivatives". 28 (2): 345–355. doi:10.1007/s11224-016-0882-y. S2CID 99796626.
^ Hindenberg, Philip; Romero-Nieto, Carlos (2016). "Phosphaphenalenes: An evolution of the phosphorus heterocycles". Synlett. 27 (16): 2293–2300. doi:10.1055/s-0035-1562506.
^ Romero‐Nieto, Carlos; López-Andarias, Alicia; Egler-Lucas, Carolina; Gebert, Florian; Neus, Jens-Peter; Pilgram, Oliver (2015). "Paving the way to novel phosphorus‐based architectures: A noncatalyzed protocol to access six‐membered heterocycles". Angew. Chem. Int. Ed. 54 (52): 15872–15875. doi:10.1002/anie.201507960. PMID 26549742.

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[Trujillo_2016-1] Trujillo, Cristina; Sánchez-Sanz, Goar; Alkorta, Ibon; Elguero, José (2017). "An insight on the aromatic changes in closed shell icosagen, tetrel, and pnictogen phenalenyl derivatives". 28 (2): 345–355. doi:10.1007/s11224-016-0882-y. S2CID 99796626.

[2] Hindenberg, Philip; Romero-Nieto, Carlos (2016). "Phosphaphenalenes: An evolution of the phosphorus heterocycles". Synlett. 27 (16): 2293–2300. doi:10.1055/s-0035-1562506.

[3] Romero‐Nieto, Carlos; López-Andarias, Alicia; Egler-Lucas, Carolina; Gebert, Florian; Neus, Jens-Peter; Pilgram, Oliver (2015). "Paving the way to novel phosphorus‐based architectures: A noncatalyzed protocol to access six‐membered heterocycles". Angew. Chem. Int. Ed. 54 (52): 15872–15875. doi:10.1002/anie.201507960. PMID 26549742.

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