Formation of Langmuir layers and surface modification using new upper-rim fully tethered bipyridinyl or bithiazolyl cyclodextrins and their fluorescent metal complexes.

Seven new amphiphilic cyclodextrins bearing bipyridyl or bithiazolyl moieties at the narrow rim and free hydroxyl or methoxyl groups at the wide rim of the cyclooctaamylose crown were synthesized using a one step "phosphine imide" approach. These ligands form metal complexes that have fluorescence properties with potentials for optical applications. Here, the cyclodextrin derivatives were used as probes for evaluating the role of different moieties in the self-assembly process, providing crucial information in creating functional devices. The behavior of these molecules and of complexes with EuIII in some cases was studied in Langmuir films using surface pressure (pi) and surface potential (deltaV) measurements performed as a function of film compression (compression isotherms). For chosen cyclodextrins, Brewster angle microscopy (BAM) in monolayers was performed. Films formed with derivatives 1, 3, 7, and 2compl were transferred on mica using the Langmuir-Blodgett technique. The properties of the films deposited on mica were analyzed with fluorimetry and, in the case of derivative 7, using fringe of equal chromatic order technique (FECO). The monolayer structure and the fluorescence properties of the Langmuir-Blodgett films indicate that the derivatives studied can be used for preparing cyclodextrin-based optical devices.