Due to the force effect, the generated three-membered ring does not have a "node", and our EX-AFIR calculations suggests that the ring-opening of this three-membered ring requires a much higher activation force of 2700 pN (Figure ). Reaction path explorations regarding the degradation of pinanediol under tensile force were also performed (see SI for details). However, though pinanediol also has a relatively low F act , from which the mechanoradicals generated are very short-lived. The force-coupled ring-opening reaction has a barrier of only 31.1 kJ/mol under F τ = 2300 pN (see Figure for the comparison of stability for mechanoradicals derived from camphanediol and pinanediol) and leads to the formation of a 1,4diradical species. This 1,4-diradical species can readily go scissile decomposition to form two alkene species. Therefore, it is very unlikely that these mechanoradicals derived from pinanediol can be experimentally observed or further utilized.