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Enhancement of Host–Guest Interactions Using Rationally Designed Macrocyclic Boronic Esters with a Naphthalene Core
Author(s) -
Kikuchi Yuji,
Takahagi Hiroki,
Ono Kosuke,
Iwasawa Nobuharu
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201301577
Subject(s) - naphthalene , stacking , chemistry , boronic acid , molecule , aromaticity , solvent , steric effects , crystallography , stereochemistry , organic chemistry
Efficient inclusion of electron‐deficient aromatic guest molecules in an organic solvent utilizing π‐stacking interactions was achieved by using two kinds of macrocyclic boronic esters, 1,4‐naph‐ [2+2] and 1,5‐naph‐ [2+2] , which were easily prepared by self‐assembly of 1,4‐naphthalenediboronic acid ( 3 ) or 1,5‐naphthalenediboronic acid ( 4 ) and racemic tetrol 1 with an indacene framework in a protic solvent. The X‐ray crystallographic analyses revealed that the tilt angles of the two naphthalene rings are different: that of 1,4‐naph‐ [2+2] is about 15° and that of 1,5‐naph‐ [2+2] is about 0°. Owing to the parallel alignment of two aromatic rings, 1,5‐naph ‐[2+2] has a much higher binding ability than 1,4‐naph‐ [2+2] . This knowledge could be useful for the design of the new host molecules in organic solvents.