Electronic Thesis and Dissertation Repository


Master of Science




Dr. James A. Wisner


In the context of hydrogen bonded materials, most efforts have been focusing on designing and synthesizing acceptor and donor arrays that in their original forms are capable of hydrogen bonding. However, less attention has been paid to the molecules that potentially act as viable acceptors or donors upon exposure to external stimuli.

This thesis describes the design, synthesis and photophysical properties of photochromic thioindigo derivatives as potential acceptors. Illumination of light can induce photoisomerization of thioindigo derivatives where they can change their orientation to generate linear hydrogen bond arrays (AAA). This linear arrangement accounts for the formation of hydrogen bonded complexes with different donor arrays (AAA-DD(D)). The stability of the complexes was determined by using 1H NMR titration procedure where the most stable complex showed a Ka of 2.3 x 10-5 M-1.