Photochromism is defined as the ability of a compound to switch between two isomeric states with each of these states having its own unique optical, structural, and electrochemical characteristics. Among the many classes of photochromic compounds, diarylethenes (DAEs) have gained attention owing to their superior fatigue resistance and potential for use as optical storage media, as sensors and probes including dosimeters, in biological applications, and for catalyst control. Recently they have gained attention as photoactive linkers in metal-organic frameworks (MOFS). We will describe the synthesis of a naphthoquinone based DAE containing thienyl aryl groups bearing terminal iodine atoms. Our synthesis relies on Suzuki coupling methodology as opposed to the traditionally utilized Stille coupling to obtain quinone DAEs. Single crystal X-ray diffraction experiments show the existence of intermolecular halogen bonding between the quinone oxygen and the thienyl iodine, the first time such an interaction has been observed in a diarylethene. Given this observation, we will discuss our attempts to make photoresponsive porous organic frameworks utilizing our photochromic DAE interfaced with imine linkers to generate halogen bonded materials.

Halogen bonding in photochromic naphthoquinone based diarylethenes

ACS Spring 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.