Development of Molecular Recognition Sensing Systems Using Frmation of Intra- and Inter-moleulcar Excimer

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We have carried out the following studies to attain our objects of the titled project.1. We have prepared gamma-cyclodextrin (gamma-CD) derivatives bearing a 1-pyrenebutyric acid (1-PBA) or a 1-pyrenecarboxylic acid (1-PA) moiety at one of primary or secondary hydroxyl groups. Among the gamma-CD derivatives gamma-CDs substituted with 1-PBA at primary hydroxyl side capable of forming a stable association dimer have been applicable to a novel sensing system with which cholic acid derivatives could be detected down to the order of muM, because they showed enormous decrease in excimer emission and increase in monomer emission. The responses for guests were found to be affected theiize, shape, and polarity.2. We have prepared three and four regioisomers of beta-and gamma-CD derivatives, respectivelty, possessing two naphthalene moieties which can form excimer intramolecularly, and revealed mutual location between the fluorophores and their orientations in and out of the CD cavity. In addition, we have carried out a basic investigation using the compounds as molecular recognizing sensors. The formation of the intramolecular excimers was affected by the addition of guest ; the excimer fluorescence of some of the CD derivatives was increased and, in others cases, the same guest weakened the excimer fluores cence with different intensities. These results suggest that fractional and simultanious detection for the compounds can be realized by using a system in which CD derivatives are involved as multipe sensor elements.3. We have prepared beta-CD derivatives bearing dansyl and ferrocene moiety acting as a flurorescence and a dichroic probes, respectively, and have revealed that they were applicable to molecular recognizing sensing sensing system. We have also found that azobenzene-modified gamma-CD whose guest binding ability can be changed by photochemical cis-trans isomerization acts as a photoswitchable muiti-response molecular recognizing sensor.