Premium
Inclusion of Two Different Guest Molecules within a Rationally Designed Macrocyclic Boronic Ester in Organic Solvent
Author(s) -
Kikuchi Yuji,
Ono Kosuke,
Johmoto Kohei,
Uekusa Hidehiro,
Iwasawa Nobuharu
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405163
Subject(s) - chemistry , boronic acid , pyrene , isothermal titration calorimetry , molecule , solvent , diol , organic chemistry , combinatorial chemistry
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.