Dynamic Formation of Noncovalent Calixsalen Aggregates

Małgorzata Petryk; Anna Troć; Błażej Gierczyk; Witold Danikiewicz; Marcin Kwit

doi:10.1002/chem.201500945

Dynamic Formation of Noncovalent Calixsalen Aggregates

Chemistry. 2015 Jul 13;21(29):10318-21. doi: 10.1002/chem.201500945. Epub 2015 Jun 17.

Authors

Małgorzata Petryk^{1

2}, Anna Troć³, Błażej Gierczyk¹, Witold Danikiewicz⁴, Marcin Kwit^{5

6}

Affiliations

¹ Department of Chemistry, Adam Mickiewicz University, Umultowska 89B, 61 614 Poznań (Poland).
² Wielkopolska Center for Advanced Technologies (WCAT), Umultowska 89C, 61 614 Poznań (Poland).
³ Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01 224, Warszawa (Poland).
⁴ Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01 224, Warszawa (Poland). witold.danikiewicz@icho.edu.pl.
⁵ Department of Chemistry, Adam Mickiewicz University, Umultowska 89B, 61 614 Poznań (Poland). Marcin.Kwit@amu.edu.pl.
⁶ Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01 224, Warszawa (Poland). Marcin.Kwit@amu.edu.pl.

PMID: 26138871
DOI: 10.1002/chem.201500945

Abstract

A procedure for studying "dynamic structural behavior" of large chiral macrocycles is presented. Ion mobility MS, diffusion-ordered NMR spectroscopy (DOSY NMR), and optical rotation (OR) measurements, supported by calculations, are used together as effective complementary methods to study dynamic formation of noncovalent aggregates. It is shown that the monomer-dimer equilibrium is driven by π-π or CH-π interactions and controlled largely by the substitution pattern of the calixsalen skeleton.

Keywords: NMR; calixsalens; ion mobility MS; optical rotation; self‐assembly.

Publication types

Research Support, Non-U.S. Gov't