1,2,3,4-Tetraphenylnaphthalene
Encyclopedia
1,2,3,4-Tetraphenylnaphthalene is a polycyclic aromatic hydrocarbon
Polycyclic aromatic hydrocarbon
Polycyclic aromatic hydrocarbons , also known as poly-aromatic hydrocarbons or polynuclear aromatic hydrocarbons, are potent atmospheric pollutants that consist of fused aromatic rings and do not contain heteroatoms or carry substituents. Naphthalene is the simplest example of a PAH...

 commonly prepared in the undergraduate teaching laboratory as an introduction to the Diels-Alder reaction, in this case between benzyne (generated in situ) and tetraphenylcyclopentadienone
Tetraphenylcyclopentadienone
Tetraphenylcyclopentadienone is a dark purple to black crystalline solid at standard temperature and pressure. Because of its highly conjugated nature, this organic compound can be analyzed in the UV spectrum. Tetraphenylcyclopentadienone has a "propeller" shape in its 3D conformation...

. It has two crystalline forms, and therefore has two different melting points.
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