The design, synthesis, and properties of isoindolinone molecular switches

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University of New Brunswick


The design, synthesis and photophysical analysis of bi- and multi- stable photoswitches based on the isoindolinone heterocycle was carried out. The design process included a rational computationally assisted modelling approach that used density functional theory and time dependent density functional theory to perform a geometry optimization on a structure of interest and predict its optical absorbance properties. If the target molecule exhibited a large separation of its absorbance profile in one isomeric form over the other, it became a synthetic target. The synthesis of three photoswitching targets was attempted but not completed. The progress towards the synthesis of two of the targets was significant, while the other was abandoned at an earlier stage. The thiophene substituted and benzothiophene substituted aryl ester intermediates from the synthetic pathway towards the isoindolinone photoswitches were discovered to have unique optical properties in solution, films and the solid state. For these reasons, the photophysical properties of the thiophene and benzothiophene substituted aryl esters were studied.