Chirality of host molecules can be induced and/or inverted
by the
guest molecules. However, the adapting chirality of hosts to the length
of n-alkanes remains a great challenge because n-alkanes are neutral, achiral, and linear molecules, resulting
in a weak interaction with most compounds. Herein, we report a system
with chirality adapted to n-alkane lengths, using
a pillar[5]arene-based macrocyclic host,
S-Br, which contains five stereogenic carbons and five terminal bromine
atoms on each rim. The electron-rich cavity of
S-Br could include n-alkanes and the planar-chiral
isomers sensitively inverted in response to the lengths of the complexed n-alkanes. The inclusion of a short n-alkane
such as n-pentane made
S-Br more inclined to be in the pS-form, whereas the
inclusion of long n-alkanes such as n-heptane made the pR-form more favorable. The difference
in the stability of the isomers was supported by the crystal structures
and the theoretical calculations. Furthermore, temperature drives
the adaptive chirality of
S-Br with n-alkanes. An n-alkane with middle length, n-hexane, showed the dominance of the pR-form of
S-Br at a higher temperature,
whereas the pS-form was shown at a lower temperature.