One-step Access to Resorcinsalens-Solvent-Dependent Synthesis, Tautomerism, Self-sorting and Supramolecular Architectures of Chiral Polyimine Analogues of Resorcinarene

Chemistry : a European Journal
Joanna SzymkowiakMarcin Kwit

Abstract

Substituted 2,4- and 4,6-dihydroxyisophthalaldehydes were condensed with optically pure and racemic trans-1,2-diaminocyclohexane to form resorcinarene-like polyimine macrocycles (resorcinsalens), the structure and stoichiometry of which were controlled by the choice of the reaction medium. Particularly, the cyclocondensation reactions were driven by the solubility, tautomerization, or by social self-sorting. The resorcinsalens crystallized as inclusion compounds, in which the guest molecules were situated either in channels or in voids. In the highly hydrated crystals of one of the [2+2] macrocycles and chloroform-solvated crystals of a [4+4] product the channels were interconnected, as in zeolites, enabling possible migration of loosely bound solvent molecules in three dimensions. The association mode depended on the structural modification of the host molecule and the type of included solvent molecule(s).

References

Sep 2, 2000·The Journal of Organic Chemistry·J GawronskiA Katrusiak
Dec 20, 2002·Angewandte Chemie·Stuart J RowanJ Fraser Stoddart
Apr 12, 2003·Advances in Colloid and Interface Science·R TuinierC G de Kruif
Oct 11, 2003·Organic Letters·Jonathan H ChongMark J MacLachlan
Jun 23, 2005·Journal of the American Chemical Society·Peter T CorbettSijbren Otto
Jan 18, 2006·The Journal of Organic Chemistry·Marc SauerMark J MacLachlan
Mar 7, 2006·Chemical Communications : Chem Comm·Leonard J Barbour
Jan 11, 2007·Chemical Reviews·Nataliya E BorisovaYuri A Ustynyuk
Sep 20, 2011·Angewandte Chemie·Kim E JelfsAndrew I Cooper
Jul 4, 2015·Chemistry : a European Journal·Małgorzata PetrykMarcin Kwit
Nov 10, 2015·Organic & Biomolecular Chemistry·Agnieszka JaniakMarcin Kwit
Dec 9, 2015·Chemistry : a European Journal·Jan JanczakJerzy Lisowski
Dec 15, 2015·Organic Letters·Przemysław KierykJerzy Lisowski
Apr 7, 2016·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Colin R GroomSuzanna C Ward
Dec 23, 2016·Angewandte Chemie·Daniel BeaudoinMichael Mastalerz

❮ Previous
Next ❯

Citations

Jul 14, 2018·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Marcin KwitJacek Gawroński
May 28, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Przemysław Starynowicz, Jerzy Lisowski
Nov 18, 2021·Inorganic Chemistry·Katarzyna ŚlepokuraJerzy Lisowski

❮ Previous
Next ❯

Related Concepts

Related Feeds

Cell Migration

Cell migration is involved in a variety of physiological and pathological processes such as embryonic development, cancer metastasis, blood vessel formation and remoulding, tissue regeneration, immune surveillance and inflammation. Here is the latest research.