Phosphaphenalenes are a class of
heterocyclicaromatic compounds containing
phosphorus with
molecular formulaC12H9P. It is related to
phenaleneC13H10, where one of its carbons is replaced by phosphorus (phenalene is a
polycyclic aromatic hydrocarbon).[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]
^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.
PMID26549742.