Force-Triggered Atropisomerization of a Parallel Diarylethene to Its Antiparallel Diastereomers

This paper describesa mechanical approach to inducingthe atropisomerizationof a parallel diarylethene into its antiparallel diastereomers exhibitingdistinct chemical reactivity. A congested parallel diarylethene mechanophorein the (R ( a ) ,S ( a ))-configuration with mirror symmetryis atropisomerized to its antiparallel diastereomers with C (2) symmetry under ultrasound-induced force field.The resulting stereochemistry-converted material gains symmetry-allowedreactivity toward conrotatory photocyclization.

Automated summary

This paper presents a mechanical approach to induce atropisomerization in a parallel diarylethene molecule, resulting in distinct chemical reactivity of its antiparallel diastereomers. Under ultrasound-induced force field, a congested parallel diarylethene mechanophore in (R(a), S(a)) configuration with mirror symmetry is atropisomerized to antiparallel diastereomers with C(2) symmetry. The obtained stereochemistry-converted material exhibits symmetry-allowed reactivity towards conrotatory photocyclization.