AI Article Synopsis
- The study introduces a photoswitchable quadruple hydrogen-bonding motif that can switch between two distinct bonding configurations (DADA and AADD), allowing for significant changes in molecular interactions.
- This molecular system involves a diarylethene compound that changes its structure upon exposure to light, leading to a dramatic decrease in its ability to form dimers by over 1000 times.
- The findings suggest that this innovative bonding motif can be utilized to control self-assembly and polymerization processes in materials science using light as a trigger.
Article Abstract
Multiple hydrogen-bonding motifs serve as important building blocks for molecular recognition and self-assembly. Herein, a photoswitchable quadruple hydrogen-bonding motif featuring near-complete, reversible, and thermostable conversion between DADA and AADD arrays associated with an alteration of their dimerization constants by over 3 orders of magnitude is reported. The system is based on a diarylethene featuring a ureidopyrimidin-4-ol moiety, which upon photoinduced ring closure and associated loss of aromaticity undergoes enol-keto tautomerization to a ureidopyrimidinone moiety. The latter causes a transformation of the hydrogen-bonding arrays and significantly weakens the free energy of dimerization in the case of the closed isomer. This photoswitchable quadruple hydrogen-bonding motif should allow us to spatially and temporarily direct self-assembly and supramolecular polymerization processes by light.
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