ABSTRACT
The ultrafast photochemistry of a new spiropyran photoswitch (Py-BIPS) has been investigated, revealing many advantages in the application in water over the previously studied spiropyrans. Functionalized Py-BIPS derivatives are presented for the study of pH dependence, stability, toxicity, and the thermal and photochemical behavior on longer time scales in aqueous media using several spectroscopic methods. These investigations pave the way for the practical use of Py-BIPS derivatives as photoswitchable ligands of biomolecules.
Subject(s)
Benzopyrans/chemistry , Indoles/chemistry , Nitro Compounds/chemistry , Photochemical Processes , Water/chemistry , Ligands , Molecular Structure , Nuclear Magnetic Resonance, BiomolecularABSTRACT
The reversible switching of a water-soluble spiropyran compound is recorded over 1 ns by means of femtosecond vis-pump/vis- and IR-probe spectroscopy under aqueous conditions. Our investigations reveal that the photochemical conversion from the closed spiropyran to the open merocyanine takes 1.6 ps whereas the reversed photoreaction is accomplished within 25 ps. The combination of time-resolved and steady-state observations allows us to reveal central parts of the reaction pathway leading to either form. The enhanced water solubility, its fast and efficient switching behavior, and its stability against hydrolysis over a time range of several weeks make this compound an attractive and versatile tool for biological applications.
