Tethering of ANS Based Fluorescent Probes to Cyclodextrin Hosts with Potential Applications as a Fluorescent Sensor

The ultimate goals of this Masters project were to synthesize a reusable, fluorescent molecular sensor and to evaluate its potential effectiveness. The molecular sensor was to be synthesized from an anilino naphthalenesulfonic acid (ANS) based fluorescent probe and a beta-cyclodextrin (beta-CD) host, either natural or modified. As a means of enhancing the effectiveness of the molecular sensor, it was determined that there should be a very large difference in intensity in the "on" and "off" positions, thus making it very easy to identify the sensors position.;Several synthetic techniques were investigated. Attempts were made to brominate 2,6-TNS and to protect the amine group of 2,6-TNS to be followed with further work to brominate the protected 2,6-TNS. These attempts were unsuccessful.;Attempts were also made to modify the CD before attaching the probe. These attempts were made with beta-CD. Investigations were made into attaching an alkyl chain, which would act as the tether between the host and guest molecules, onto the larger secondary rim of beta-CD, but attempts to do so were unsuccessful. Investigations were also made into modifying the primary rim of beta-CD. beta-CD was successfully mono-tosylated.;The mono-tosylated beta-CD was reacted with 2,6-TNS and evidence suggests that the host and guest molecules are tethered via a single carbon alkyl chain.;Intermolecular studies were conducted involving several different ANS based fluorescent probes and dimethyl-beta-CD and beta-CD. It was identified that 2-toluidino 6-naphthalenesulfonic acid (2,6-TNS) would be the most effective probe to use due to its strong affinity to form inclusion complexes with beta-CDs and the very large increase in fluorescence emission intensity upon inclusion.