Synthesis, crystal structure, and luminescence of tetrakis (4-methoxyphenyl)methane
authors Guieu, S; Rocha, J; Silva, AMS
nationality International
journal TETRAHEDRON LETTERS
author keywords Fluorescence; Trityl luminophore; Solid state luminescence; Single X-ray crystallography; Crystallization-induced phosphorescence
keywords HYDROGEN-BONDED NETWORKS; MOLECULAR TECTONICS; TETRAPHENYLMETHANE; TETRAPHENYLSILANE; EMISSION; SYMMETRY; SYNTHON
abstract A new synthesis of a tetrahedral tecton, tetrakis(4-methoxyphenyl)methane, is reported. This compound exhibits a strong fluorescence around 340 nm at room temperature, both in solution and in the solid state. Upon crystallization, another luminescence band can be observed around 500 nm, attributed to phosphorescence. A study of the single-crystal structure of the compound provided a rationalization of this crystallization induced phosphorescence. The crystal of tetrakis(4-methoxyphenyl)methane belongs to the tetragonal space group P (4) over bar2(1)c, and the structural analysis revealed a close packing of the molecules, with no void space and no solvent molecules in the crystal. The molecules are held together in a columnar array via multiple C-H center dot center dot center dot pi it hydrogen bonds. The hydrogen bonds between the molecules impede the torsional vibrations of the aromatic rings, preventing thermal relaxation from the triplet state, and hence promoting phosphorescence at room temperature. (C) 2013 Elsevier Ltd. All rights reserved.
publisher PERGAMON-ELSEVIER SCIENCE LTD
issn 0040-4039
year published 2013
volume 54
issue 22
beginning page 2870
ending page 2873
digital object identifier (doi) 10.1016/j.tetlet.2013.03.104
web of science category Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000318664900030
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journal impact factor 2.125
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