258274-17-8Relevant articles and documents
Extended structures built on a triphenoxymethane platform - C3- symmetric, conformational mimics of calix[n]arenes
Dinger, Maarten B.,Scott, Michael J.
, p. 2467 - 2478 (2000)
A series of C3-symmetric tris(3,5-dialkyl-2-hydroxyphenyl)methanes (alkyl = tert-butyl, methyl, tert-pentyl) have been synthesized in high yield from their respective phenols and fully characterized, including single crystal X-ray structures for two examples. The di-tert-butyl-substituted compound, 1a, has been derivatized to a tris-acid chloride, 4, which was treated with a variety of amines (dimethylamine, benzylamine, glycine, and alanine) from which the corresponding trisamides 5-8 were formed. The absolute geometry and conformation of the dimethylamine, glycine, and alanine derived systems were determined by X-ray analyses, and in all cases, the three phenolate arms point up with respect to the central methine. Alkali metal binding studies (Li, Na, K, Rb, and Cs) were carried out for the dimethylamine, benzylamine, and glycine compounds 5-7, and these compounds were found to have some selectivity for potassium cations. NMR studies demonstrate that C3 symmetry is retained in all the compounds and the stoichiometry for lithium ion complexation is 1:1, whereas two ligands are needed to complex sodium cations. Crystal structures of the dimethylamine derivative with lithium picrate and the benzylamine and glycine derivatives with sodium tetraphenytborate were also determined.
