An Enantiopure Hydrogen-Bonded Octameric Tube: Self-Sorting and Guest-Induced Rearrangement

Dovilė Račkauskaitė; Rokas Gegevičius; Yutaka Matsuo; Kenneth Wärnmark; Edvinas Orentas

doi:10.1002/anie.201508362

An Enantiopure Hydrogen-Bonded Octameric Tube: Self-Sorting and Guest-Induced Rearrangement

Angew Chem Int Ed Engl. 2016 Jan 4;55(1):208-12. doi: 10.1002/anie.201508362. Epub 2015 Nov 5.

Authors

Dovilė Račkauskaitė¹, Rokas Gegevičius¹, Yutaka Matsuo², Kenneth Wärnmark³, Edvinas Orentas⁴

Affiliations

¹ Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius (Lithuania).
² Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan).
³ Center for Analysis and Synthesis, Department of Chemistry, Lund University, P.O. Box 124, 22100 Lund (Sweden).
⁴ Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius (Lithuania). edvinas.orentas@chf.vu.lt.

PMID: 26537418
DOI: 10.1002/anie.201508362

Abstract

The assembly of a discrete hydrogen-bonded molecular tube from eight small identical monomers is reported. Tube assembly was accomplished by means of selective heterodimerization between isocytosine and ureidopyrimidinone hydrogen-bonding motifs embedded in an enantiopure bicyclic building block, leading to the selective formation of an octameric supramolecular tube. Upon introduction of a fullerene guest molecule, the octameric tube rearranges into a tetrameric inclusion complex and the hydrogen-bonding mode is switched. The dynamic behavior of the system is further explored in solvent- and guest-responsive self-sorting experiments.

Keywords: fullerenes; hydrogen bonds; inclusion compounds; self-sorting; supramolecular chemistry.

Publication types

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