62477-06-9Relevant academic research and scientific papers
Supramolecular Assembly of Tris(4-carboxyphenyl)arenes: Relationship between Molecular Structure and Solid-State Catenation Motifs
Lai, Holden W.H.,Wiscons, Ren A.,Zentner, Cassandra A.,Zeller, Matthias,Rowsell, Jesse L.C.
, p. 821 - 833 (2016/02/18)
The crystal structures of seven 1,3,5-tris(4-carboxyphenyl)arenes with functionalized central arene rings are reported. The formation of (6,3) hcb hexagonal sheets as a result of carboxylic acid dimer formation was observed in most of the crystal structures, with the exception of two compounds with functional groups capable of forming hydrogen bonds, namely, 2,4,6-tris(4-carboxyphenyl)-1,3-diaminobenzene and 2,4,6-tris(4-carboxyphenyl)-3-methylaniline. These structures were found to incorporate THF solvent molecules in their hydrogen-bonding motif, giving rise to distorted pseudohexagonal arrays. Functional groups on the central ring were found to influence stacking distances, stacking offsets, inclination angles, degree of catenation, and dimensions of solvent-occupied channels. To better understand and appreciate these complicated crystal structures, they were categorized into four distinct stacking/catenation families: simple stacking, single-layer offset catenation, double-layer offset catenation, and rotated-layer catenation. The unique structure of the unfunctionalized parent compound 1,3,5-tris(4-carboxyphenyl)benzene is rationalized in light of the structural behavior of its derivatives.
Orthohalogen substituents dramatically enhance hydrogen bonding of aromatic ureas in solution
Giannicchi, Ilaria,Jouvelet, Benjamin,Isare, Benjamin,Linares, Mathieu,Dalla Cort, Antonella,Bouteiller, Laurent
supporting information, p. 611 - 613 (2014/01/06)
The phenylurea moiety is a ubiquitous synthon in supramolecular chemistry. Here we report that the introduction of chlorine or bromine atoms in the ortho positions to the urea unit is a simple and very efficient way to improve its intermolecular hydrogen bond (HB) donor character. This effect was demonstrated in solution both in the context of self-association of bis-ureas and hydrogen bonding of mono-ureas to strong HB acceptors. The Royal Society of Chemistry 2014.
Synthesis of aza-m-xylylene diradicals with large singlet-triplet energy gap and statistical analyses of their EPR spectra
Olankitwanit, Arnon,Pink, Maren,Rajca, Suchada,Rajca, Andrzej
supporting information, p. 14277 - 14288 (2014/12/11)
We describe synthesis and characterization of a derivative of aza-m-xylylene, diradical 2, that is persistent in solution at room temperature with the half-life measured in minutes (～80-250 s) and in which the triplet ground state is below the lowest sing
Synthesis of Polyfunctionalized Biphenyls as Intermediates for a New Class of Liquid Crystals
Manka, Jason T.,Guo, Fengli,Huang, Jianping,Yin, Huiyong,Farrar, John M.,Sienkowska, Monika,Benin, Vladimir,Kaszynski, Piotr
, p. 9574 - 9588 (2007/10/03)
A series of hexa- and octasubstituted biphenyls containing halogen, amino, nitro, and propylthio substituents were prepared by metal-mediated convergent synthesis from halobenzene precursors. The Pd-assisted C-C coupling methods were ineffective in the fo
A convenient and efficient synthesis of polyphenylmono-, di-, and -triaminobenzenes
Miura,Oka,Momoki
, p. 1419 - 1422 (2007/10/02)
A new convenient and efficient synthesis of polyphenylmono- and -diaminobenzenes by the palladium(0)-catalyzed cross-coupling reaction of polyhalomono- and -diaminobenzenes with phenylboronic acid is described. A synthesis of 2,4-diphenyl-1,3,5-triaminobe
