Structural Effects on Mechanochemical Reactivity of Anthracene–Maleimide Diels–Alder Adducts

• DOI: 10.1021/acs.macromol.4c00214
• Publication Date: 2024-03-27T13:39:22Z
• Authors: Tong Xie; Zheng Li; Yecheng Zhou; Bin Xi; Yuanchao Li
• Keywords: Maleimide; Diels–Alder reaction; Reactivity

Structure–activity relationship of mechanophores has always been a research focus in the field polymer mechanochemistry. Here, we report our investigation effects substitution and pulling geometry on mechanochemical reactivity anthracene–maleimide Diels–Alder (DA) adducts. The results both ultrasonication experiments constrained geometries simulate external force (CoGEF) calculations show that adducts with same points at 9-position anthracene N atom succinimide but different substituents (e.g., H, alkylthio, or dialkylamino) C2 position can be mechanochemically activated undergo retro-DA reaction under applied similar reactivity, implying an insignificant effect reactivity. Remarkably, adduct one changed from to substituent becomes inert due weak coupling associated poor orientational alignment between "scissile" bond vector.