Background
Molecules of tetrahedral symmetry, such as tetraphenylmethane (TPM) and its various analogues (sometimes quite distant) over the years, were amongst the most exploited models in crystal engineering. For example, phenyl embraces, which are cooperative supramolecular motifs composed by set of Csingle bondH ⋯ π attractive interactions have been recognized as fundamental interactions responsible for dense crystal packing of tetrahedrally-shaped species such as tetraphenylphosphonium, tetraphenylarsonium, and tetraphenylborate compounds. Another example of the significant role of TPM-like molecules is the introduction and development of molecular tectonics. Molecular tectonics is a strategy for the predictable construction of crystalline arrays from molecules called tectons. An inextricable feature of any tecton molecule is its shape and binding abilities enforce specific and directional arrangements of the same or complementary molecules[1].
Description
Tetraphenylmethane (TPM) is an organic alkane compound formed by replacing the hydrogen atoms of methane with benzene rings. TPM is an important optoelectronic material, primarily used in the preparation of OLED materials and light-emitting devices. Bipolar tetraphenylmethane derivatives prepared with TPM as the core structure carry both hole-transfer and electron-transfer units, significantly enhancing the molecule's vitrification ability and improving its luminescence performance
[2].
Chemical Properties
white to pink powder or needles
Uses
Tetraphenylmethane is used to prepare a tetrapyridone tecton, which forms a diamondoid network with large internal chambers. It is also used in the preparation of 1-{4-[tris-(4-acetyl-phenyl)-methyl]-phenyl}-ethanone by Friedel-Crafts acylation reaction with acetyl chloride using aluminum chloride as catalyst.
References
[1] Zarba, Jan K. “Tetraphenylmethane and tetraphenylsilane as building units of coordination polymers and supramolecular networks – A focus on tetraphosphonates.” Inorganic Chemistry Communications 86 (2017): Pages 172-186.
[2] YEH H, JAN L, LEE R J, et al. Glassy charge-transporting and electroluminescent tetraphenylmethane-based molecules for organic light-emitting devices[J]. SPIE Optics + Photonics, 2001, 28 1: 0. DOI:10.1117/12.416914.
