A1 Journal article (refereed)
Bis-Phenol A Cyclophanes: Synthesis, Crystal Structures and Binding Studies (2001)

Nissinen, Maija, Antonella Dalla, Amabile, Stafania, Cort, Mandolini, Luigi, Rissanen, Kari. (2001). Bis-Phenol A Cyclophanes: Synthesis, Crystal Structures and Binding Studies. Journal of Inclusion Phemomena and Macrocyclic Chemistry, 39, 229-234. https://doi.org/10.1023/A:1011174213426

JYU authors or editors

Publication details

All authors or editors: Nissinen, Maija; Antonella Dalla; Amabile, Stafania; Cort, Mandolini, Luigi; Rissanen, Kari

Journal or series: Journal of Inclusion Phemomena and Macrocyclic Chemistry

Publication year: 2001

Volume: 39

Pages range: 229-234

Publication country: Netherlands

Publication language: English

DOI: https://doi.org/10.1023/A:1011174213426

Publication open access: Not open

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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.

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