Search results for "merocyanine"
showing 7 items of 7 documents
Density Functional Theory Study of the Trans-Trans-Cis (TTC)→Trans-Trans-Trans (TTT) Isomerization of a Photochromic Spiropyran Merocyanine
2008
Density Functional Theory (DFT) calculations have been performed on the TTC→TTT isomerization reaction of the open forms of the 1',3'-dihydro-8-bromo-6-nitro- 1',3',3'-trimethylspiro[2H-1-benzopyran-2,2'-(2H)indole (8-Br-6-nitro-BIPS) system. The calculations were carried out in vacuo and in methylene chloride solution at different temperatures. Results are compared with the available experimental values of free energy difference and activation energy in solution.
Ultrafast Photo-Dynamics of a Reversible Photochromic Spiropyran
2002
We report the first ultrafast ring closure kinetics of the merocyanine (MC) of a reverse photochromic spiropyran 1‘,3‘,3‘-trimethyl-6,8-dinitrospiro[2H-1-benzopyran-2,2-indoline] (6,8-dinitro BIPS) and its 1‘-(2-carboxyethyl) substituted derivative. The reaction is fast and essentially over in a few hundred picoseconds. The rate of MC-S1 state decay evaluated from transient absorbance can be correlated directly with the MC-S1 state lifetime as determined using stimulated and ordinary emission measurements. The recovery of the MC-S0 state from MC-S1 has a component with a lifetime of 60−78 ps in acetonitrile with a second component of 350−470 ps probably due to a metastable intermediate. We …
Factors affecting the amount and the mode of merocyanine 540 binding to the membrane of human erythrocytes. A comparison with the binding to leukemia…
1995
Abstract In the presence of albumin Merocyanine 540 (MC540) exhibits a very limited binding to the outer surface of the membrane of normal erythrocytes, whereas pronounced binding is observed to leukemia cells. To find out whether this difference is due to differences in the composition or structural organization of the cell membrane we analyzed effects of a number of covalent and non-covalent perturbations of the red cell membrane on the binding and fluorescence characteristics of membrane-bound MC540. It is shown that exposure of the cells to cationic chlorpromazine, neuraminidase or photodynamic treatment with AlPcS 4 as sensitizer caused a limited increase (30–50%) of MC540 binding, tog…
Ultrafast ring-opening/closing and deactivation channels for a model spiropyran-merocyanine system.
2011
The photochemistry of a model merocyanine-spiropyran system was analyzed theoretically at the MS-CASPT2//SA-CASSCF(14,12) level. Several excited singlet states were studied in both the closed spiropyran and open merocyanine forms, and the paths to the different S(1)/S(0) conical intersections found were analyzed. After absorption of UV light from the spiropyran form, there are two possible ultrafast routes to efficient conversion to the ground state; one involves the rupture of the C(spiro)-O bond leading to the open form and the other involves the lengthening of the C(spiro)-N bond with no photoreaction. From the merocyanine side the excited state can reach a very broad S(1)/S(0) conical i…
Ground- and First-Excited-Singlet-State Electric Dipole Moments of Some Photochromic Spirobenzopyrans in Their Spiropyran and Merocyanine Form
2002
The dipole moments of four photochromic derivatives of indolinospirobenzopyran have been studied in their spiro and their open merocyanine form, in dioxane. Determinations have been done by electrooptical absorption measurements (EOAM). To prepare either a pure spiropyran or a pure merocyanine form solution, the experimental setup had to be modified by addition of a second light beam. In this way thermal equilibration between the spiropyran and the merocyanine form and switching from one form to the other induced by the measuring light beam could be avoided. The ground-state dipole moment of the spiro form amounts to (10−15) × 10-30 C m and increases strongly to about 60 × 10-30 C m with th…
Theoretical study of spiropyran-merocyanine thermal isomerization.
2004
Abstract Quantum mechanical computations at DFT level were carried out on the processes involved in the thermal reaction SP ⇆ ME, where SP is the nitro-substituted spirobenzopyran (1 ′ ,3 ′ -dihydro-1 ′ ,3 ′ ,3 ′ -trimethyl-6-nitro-spiro[2H-1-benzopyran-2,2 ′ - [2H]indole]) in the closed form and ME is the corresponding open form. A detailed theoretical description of the overall reaction is reported along with the thermodynamic parameters for all intermediates and transition states. The obtained activation energy value is in agreement with the available experimental data in solution.
Control of the thermal reaction of a photochromic spirobenzopyran by the enzyme-like activity of albumins
1997
Abstract The thermal ring-opening reaction of a negative photochronic spirobenzopyran was investigated in the presence and absence of albumins. In the presence of the proteins, the formation of the merocyanine form from the spiro form is enhanced markedly by two orders of magnitude. The results for five different albumins indicate the enzyme-like activity of the proteins. The influence of pH, temperature and various ligands was examined in detail for bovine serum albumin (BSA) and human serum albumin (HSA). In particular, it was deduced that warfarin shows reversible purely competitive inhibition for BSA with an inhibitor constant K 1 of 1.6×10 −3 M. The results suggest that the catalytic c…