Click addition; mechanophore; polymer mechanochemistry; single-molecule force spectroscopy; spirothiopyran; Cycloreversion; Maleimides; Mechano-chemistry; Ring opening; Self reinforcing; Single molecule force spectroscopy; Single molecule level; Single-molecule observation; Atomic and Molecular Physics, and Optics; Materials Science (all); Condensed Matter Physics; Electrical and Electronic Engineering; General Materials Science
Abstract :
[en] Spirothiopyran (STP) is particularly attractive when used as a mechanophore to endow polymers with both damage-signaling and self-reinforcing capacity. It is, however, not clear the actual force required to induce the cycloreversion of STP into ring-opened thiomerocyanine (TMC), which reacts spontaneously with activated C-C bonds. Here, we used atomic force microscopy (AFM)-based single molecule force spectroscopy (SMFS) to study the mechanochemistry of STP mechanophore. It is found that the ring-opening of STP at room temperature requires forces of ∼ 200–400 pN, depending on the pulling speed. In addition, the reversibility of STP to TMC isomerization is demonstrated. Finally, mechanochemically induced intermolecular Click addition is achieved in single molecule level by pulling STP in the presence of maleimide. [Figure not available: see fulltext.]
Disciplines :
Chemistry
Author, co-author :
Yao, Ruixiang; State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, China
Li, Xun ; State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, China ; Molecular Systems Research Unit, University of Liège, Liège, Belgium
Xiao, Nan; Department of Chemistry, College of Chemistry and Engineering, Xiamen University, Xiamen, China
Weng, Wengui; Department of Chemistry, College of Chemistry and Engineering, Xiamen University, Xiamen, China
Zhang, Wenke; State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, China
Language :
English
Title :
Single-molecule observation of mechanical isomerization of spirothiopyran and subsequent Click addition
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