Inclusion of two different guest molecules within a rationally designed macrocyclic boronic ester in organic solvent

Yuji Kikuchi; Kosuke Ono; Kohei Johmoto; Hidehiro Uekusa; Nobuharu Iwasawa

doi:10.1002/chem.201405163

Inclusion of two different guest molecules within a rationally designed macrocyclic boronic ester in organic solvent

Chemistry. 2014 Nov 24;20(48):15737-41. doi: 10.1002/chem.201405163. Epub 2014 Oct 21.

Authors

Yuji Kikuchi¹, Kosuke Ono, Kohei Johmoto, Hidehiro Uekusa, Nobuharu Iwasawa

Affiliation

¹ Department of Chemistry, Tokyo Institute of Technology and JST-CREST, 2-12-1, O-okayama, Meguro-ku, Tokyo 152-8551 (Japan).

PMID: 25336243
DOI: 10.1002/chem.201405163

Abstract

The inclusion of two different guest molecules in a macrocyclic boronic ester in organic solvent utilizing only π-stacking interactions has been successfully realized. For this purpose, a new tetrol which has an appropriate distance between two 1,2-diol units for the inclusion of two aromatic molecules is designed and synthesized. Simple mixing of the new tetrol with 2,7-pyrenediboronic acid in the presence of pyrene-4,5-quinone efficiently affords the desired macrocyclic boronic ester, which is found by (1)H NMR spectroscopy, ESI-MS, and isothermal titration calorimetry studies to include one molecule each of a dinitronaphthalimide derivative and pyrene. Furthermore, inclusion of two planar molecules within the macrocyclic boronic ester is revealed by X-ray analysis.

Keywords: boronic esters; host-guest systems; self-assembly; supramolecular chemistry; π-stacking interactions.