merocyanine-dye and cucurbit(8)uril

A water-soluble two-dimensional supramolecular organic framework (2D SOF) was prepared via self-assembly of cucurbit[8]uril (CB[8]) and a three-arm flat linker molecule, which contains a benzene ring as the core and three Brooker's merocyanine (BM) analogs as arms. The strong host-guest interactions between BM and CB[8] and the directional head-to-tail stacking modes between the BM arms synergistically led to the formation of a 2D SOF. The structure of the 2D SOF was verified by

Topics: Benzopyrans; Bridged-Ring Compounds; Cryoelectron Microscopy; DNA; HeLa Cells; Humans; Imidazoles; Indoles; Macromolecular Substances; Microscopy, Atomic Force; Microscopy, Confocal; Water

The effect of inclusion complex formation on the photochromic behavior of a spirobenzopyran dye and its merocyanine isomer was studied in aqueous solution using cucurbit[8]uril (CB8) as a host. The merocyanine (MC) and protonated merocyanine (MCH(+)) were the most stable forms both in water and inside the cavity of CB8. The equilibrium constant of 1:1 complexation with CB8 was found to be 1.7 × 10(5) and 2.0 × 10(6) M(-1) for the former and latter species, respectively. The encapsulation led to significant change in the rate of the photoinduced and thermal photochromic transformations and hindered the hydrolysis of MC. The effect of CB8 on the reaction kinetics strongly altered with pH. The transition from the spiropyran form to trans-MC in a thermal reaction had 33 kJ mol(-1) lower activation energy and more than 5 orders of magnitude smaller Arrhenius pre-exponential factor in CB8 than in water.

Topics: Benzopyrans; Bridged-Ring Compounds; Hydrogen-Ion Concentration; Hydrolysis; Imidazoles; Indoles; Isomerism; Kinetics; Nitro Compounds; Temperature; Water