Fluorescent pyrrolinone-modified beta- and gamma-cyclodextrins (beta-1 and
gamma-1, respectively) have been synthesized as a fluorescent chemo-sensor
for organic compounds such as terpenoids and bile acids. The host compounds
show a pure monomer fluorescence around 472 nm, the intensity of which dec
reased when 1-adamantanecarboxylic acid, p-aminobenzoic acid, benzoic acid,
phthalic acid or cyclohexanecarboxylic acid were used as a guest in an aqu
eous solution of pH 5.90. On the other hand, in Menzel buffer solution of p
H 9.09, the fluorescent intensity is increased by accommodation of these gu
est molecules. The increase was seen with other guests such as terpenoids,
amino compounds and sodium bile acid salts in a Menzel buffer solution. The
extent of fluorescence variation with a guest is employed to display the c
hemo-sensor ability of these hosts. The sensing parameter (Delta I/I-0) was
used to show the sensing ability of those hosts. Hosts beta-1 and gamma-1
exhibit higher sensing ability for amines in a host solution of pH 5.90 tha
n those in a host solution of Menzel buffer. It is probably caused by some
hydrogen bonding between the carboxylic anion of the hosts and quaternary a
mmonium type guests.