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Porous Molecular Capsules as Non‐Polymeric Transducers of Mechanical Forces to Mechanophores
Author(s) -
Jędrzejewska Hanna,
Wielgus Ewelina,
Kaźmierski Sławomir,
Rogala Halina,
Wierzbicki Michał,
Wróblewska Aneta,
Pawlak Tomasz,
Potrzebowski Marek J.,
Szumna Agnieszka
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904024
Subject(s) - covalent bond , mechanochemistry , polymer , breakage , molecule , materials science , macromolecule , porosity , chemical engineering , solvent , chemistry , nanotechnology , polymer chemistry , organic chemistry , composite material , biochemistry , engineering
Mechanical grinding/milling can be regarded as historically the first technology for changing the properties of matter. Mechanically activated molecular units (mechanophores) can be present in various structures: polymers, macromolecules, or small molecules. However, only polymers have been reported to effectively transduce energy to mechanophores, which induces breakage of covalent bonds. In this paper, a second possibility is presented—molecular capsules as stress‐sensitive units. Mechanochemical encapsulation of fullerenes in cystine‐based covalent capsules indicates that complexation takes place in the solid state, despite the fact that the capsules do not possess large enough entrance portals. By using a set of solvent‐free MALDI (sf‐MALDI) and solid‐state NMR (ss‐NMR) experiments, it has been proven that encapsulation proceeds during milling and in this process hydrazones and disulfides get activated for breakage, exchange, and re‐forming. The capsules are porous and therefore prone to collapse under solvent‐free conditions and their conformational rigidity promotes the collapse by the breaking of covalent bonds.