Design, synthesis, and investigation of a visible light-driven photo-switching macromolecule

Abstract

The application of azobenzene (AZO) as a kind of photo-switch is restricted by its excitation source, i.e., UV light. Hence, visible light-driven azobenzene-based photo-switching is needed and has been designed in the work. In order to forecast the optimal triggered wavelength, the electrostatic potential, theoretical UV-vis spectra, as well as the energy gap for focused structures was calculated to describe the energy and orbit status of the molecules by DFT. According to the theoretical optimization results, m-Methyl Red (m-MR) containing copolymer was successfully synthesized as a visible light-driven photo-switch. Further, for performance evaluation, the efficiency and effectiveness of different excitation wavelengths was firstly evaluated for the copolymer using m-MR and m-Methyl Red acrylic anhydride (m-MRAA) as the controls. Compared with m-MR and m-MRAA, the copolymer exhibited outstanding characteristics as a photo-switch according to its response–recovery behavior. At the same time, blue light proved to be the most efficient excitation light source. Moreover, the equilibrium response time and recovery time showed some dependence on the excitation wavelength. Secondly, the influence of the light intensity on the isomerization transition was investigated. A relatively low light density could lead to a relatively low degree of the final cis form and needed more equilibrium time for trans to cis transformation but showed little effect on the recovery process. Thirdly, repeatable on/off irradiation was used to evaluate the fatigue resistance of the copolymer. Good fatigue resistance without photobleaching was verified from the results. Fourthly, the influence of the solvent on visible light-driven isomerization was also evaluated. Finally, the synthesized copolymer still had the characteristic of a pH indicator with a critical point at pH 5.0 and exhibited an obvious fluorescent characteristic.