Calixarene ethoxycarbonyl ester is synthesized and used as a host mole
cule in optical detection of 2-phenethylamine. A plasticized poly(viny
l chloride) membrane containing the calixarene and a fluorescent dye r
esponds to 2-phenethylamine reversibly, and the sensitivity of an opto
de is increased by substitution of the ethoxycarbonyl ester for a hydr
oxy group in calixarene. However, a large interference response to pH
is observed when the membrane contains calixarene. A phenolic proton i
s dissociated with an increase of pH, and fluorescence from the membra
ne is quenched by deprotonated calixarene, which causes the interferen
ce response to pH. The guest molecule of 2-phenethylamine is incorpora
ted inside the calixarene, and the proton dissociation in calixarene o
ccurs upon complexation. It results in the optode response to the gues
t molecule. The response to alkyl ammonium ions is also investigated,
and the selectivity of the optide is discussed.