The synthesis of calixarene L1 is described. This molecular sensor incorporates a fluorescent naphthyl moiety, the necessary fluorophore for optical transduction, whose fluorescent intensity alters to differing degrees on binding of enantiomers. Means of distinguishing between enantiomers of a chiral molecule are of critical importance in many areas of analytical chemistry and biotechnology, particularly in drug design and synthesis. Fluorescent quenching studies of calixarene L1 in methanol demonstrated no enantiomeric selectivity in a short chain amino acid, phenylglycinol, while excellent selectivity was observed for a longer chain, phenylalaninol. Fluorescent lifetime studies of this calixarene with phenylalaninol guests confirmed that a static quenching mechanism is responsible for the decrease in fluorescence intensity of L1 in methanol upon addition of phenylalaninol. Calix[4]arenes are well-known to possess ion-binding properties. The formation of metal ion complexes of the p-allyl calix[4]arene propranolol amide derivative is shown to induce a more regular and rigid cone conformation in the calix[4]arene macrocycle, which generates a significant enhancement in the observed enantiomeric discrimination. The effect of solvent on the fluorescent properties of this calixarene has been studied with regard to methanol, acetonitrile and chloroform. While enantiomeric selectivity is observed in methanol, no discrimination is achieved in acetonitrile, and although there appears to be a 1:1 association with the guest in the latter solvent, in the case of methanol the guest must be far in excess of the host to achieve enantiomeric discrimination. Upon addition of the R-enantiomer of the guest in chloroform a new band is formed, which would suggest a charge transfer complex between this guest and the calixarene, an effect, which is not observed with the S-enantiomer. Fluorescence lifetime studies in chloroform indicate a static quenching mechanism of L1 by both enantiomers of phenylalaninol, which would suggest that exciplex formation is not responsible for the new band at 440nm upon addition of Rphenylalaninol. This new band has been attributed to the presence of two different conformations of calixarene L1, which is reinforced by the 1H-NMR studies and molecular modelling studies in chapter 4. After the successful performance of calixarene L1 with respect to enantiomeric discrimination (chapters 3, 4 and 5), an attempt was made to prepare a series of calixarene sensor molecules that possess similar properties to L1, but are prepared from inexpensive starting materials. Using DCC as a coupling agent to form amides directly from calixarene tetra-acids does not however, achieve tetra-substituted amides. An alternative route was taken to produce calixarene tetra-amides which involved two steps: 1 . formation of the amide moiety 2. attachment of amide moieties to calixarene backbone The first of these two steps was carried out successfully and led to the formation of three amide subunits however the second step suffered from partial substitution, and resulted in a series of mono-, di- and tri-substituted fluorescent calixarenes. A fivefold excess of the amide moiety was used which is not sufficient to complete the tetra-substitution.