Bis-phenol A Cyclophanes: Synthesis, Crystal Structures and Binding Studies View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2001-04

AUTHORS

Maija Nissinen, Antonella Dalla Cort, Stefania Amabile, Luigi Mandolini, Kari Rissanen

ABSTRACT

The synthesis and structural characterisation of three new macrocyclicbis-phenol A cyclophane ethers are described. The solid state structuresof two of the cyclophanes were determined by single crystal X-raydiffraction. Cyclophane 3 crystallises in the orthorhombic spacegroup Pbca with unit cell dimensions of a = 11.533(7), b = 29.383(8),c = 14.927(8) Å and cyclophane 4 in the monoclinic spacegroup P21/n with cell dimensions of a = 11.585(4), b = 11.839(2), c = 18.866(2) Å, β = 94.48(2)°.The X-ray crystalstructures reveal distorted conformations, thus supporting the weak bindingof quats in solution observed by the NMR studies. In the crystalline state bothmacrocycles were found to form self-complementary dimers held together byweak intermolecular π-π and CH-π interactions. The bindingbehaviour towards a series of tetralkylammonium cations was determinedby 1H NMR titration in CDCl3 solution. The interactions between the hosts and the quats were clearly detectable but too weak to be translated into meaningful equilibrium constants. More... »

PAGES

229-234

Identifiers

URI

http://scigraph.springernature.com/pub.10.1023/a:1011174213426

DOI

http://dx.doi.org/10.1023/a:1011174213426

DIMENSIONS

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