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Fig. 2.2 Structures of five representative alkyl-substituted Q[5]s: a Me 10 Q[5]; b DMeQ[5];
c 1,2,4-HMeQ[5]; d PMeQ[5] and e CyH 5 Q[5]
Fig. 2.3 X-ray crystal structures of molecular capsules and molecular bowls of Q[5] with var-
ious metal ions: a alkali (K
+
); b alkaline earth (Ba 2 +
); c transition (Cd 2 +
); and d lanthanide
(La 3 +
) metal ions
(1,2,4-HMeQ[5]), pentamethylcucurbit[5]uril (PMeQ[5]), pentacyclopentanocuc
urbit[5]uril (CyH 5 Q[5]), and so on show no obvious difference in affinity to the
metal ions (Fig. 2.2 ).
For example, a series of molecular capsules or molecular bowls of Q[5] with
various metal ions, including alkali (K + ), alkaline earth (Ba 2 + ), transition (Cd 2 + ),
and lanthanide (La 3 + ) metal ions (Fig. 2.3 ) [ 17 , 18 ]. Moreover, these Q[5]-based
complexes exhibited the remarkable property of encapsulating a negatively
charged ion. Its easy synthesis, rigid structure, and chemical and thermal stability
could make Q[5] very attractive for complexation of anions in aqueous solution
[ 18 ]. Further experiments reveal that Q[5] shows special selectivity for including
“naked” chloride anion or nitrate anion under certain conditions. The metal-free
host has been demonstrated to selectively include nitrate ion, whereas the lantha-
nide-capped molecular capsule showed preference toward the inclusion of chloride
ion (Fig. 2.4 ) [ 19 ].
Our group synthesized complexes of alkyl-substituted Q[5]s (referring to
Fig. 2.2 ) with various metal ions. Most of them were molecular bowls or molecu-
lar capsules. The metal ions included alkali [ 12 , 13 ], alkaline earth [ 14 ], transi-
tion [ 15 ], and lanthanide [ 16 ] metal ions. For example, we evaluated the effect of
a series of alkaline earth metal ions (Ca 2 + , Sr 2 + , and Ba 2 + ) on their complexes
with CyH 5 Q[5] by mixing their chloride salts with CyH 5 Q[5] [ 20 ]. The experi-
mental results revealed that coordination of CyH 5 Q[5]-based molecular capsules
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