Spectroscopic properties of cyclophane/anthracene and cyclophane/9-fluorenone complexes in dichloromethane

Host/guest interactions of cyclophane/anthracene (C/A) and cyclophane/9-fluorenone (C/F) complexes in dichloromethane, where the cyclophane molecule is the host, are investigated. The stability constants, log Ka, for the C/A and C/F complexes are determined by absorption and fluorescence spectroscopy. For the C/A system, log Ka is 4.2±0.2 as determined from absorption (at 325 nm) and emission (at 382, 403 and 427 nm) spectroscopic data. The analogous measurements yield 3.6±0.2 from absorption (at 309 nm) and emission (at 505 nm) spectroscopic data for the C/F system. Heats of formation of these complexes were determined by measuring the complex association constants at 25, 29 and 32 °C. These results reveal that binding of the anthracene guest by this cyclophane molecule is thermodynamically favored over that for a 9-fluorenone guest. Excited state lifetimes of these systems are also determined.