Mechanochemical Triggers for Self -Healing Polymers
Hickenboth, Charles Robert
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https://hdl.handle.net/2142/84247
Description
Title
Mechanochemical Triggers for Self -Healing Polymers
Author(s)
Hickenboth, Charles Robert
Issue Date
2006
Doctoral Committee Chair(s)
Moore, Jeffrey S.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Engineering, Materials Science
Language
eng
Abstract
Mechanochemical triggers based on the electrocyclic ring opening of both trans and cis substituted benzocyclobutenes was studied. The products of mechanically-accelerated ring opening were studied by trapping experiments. Ultrasound induces ring opening at 10°C, whereas thermal activation only took place at temperatures over 105°C. It was found that the substitution pattern around the four-membered ring influenced the rotational preference for ring opening. 13C labeling studies indicate that while the trans isomer prefers to open in a conrotatory manner, the cis isomer prefers to open in a disrotatory manner. It is proposed that these rotational preferences are a result of the efficiency of stress release; mechanical activation is greatest for those pathways which most efficiently relieve the applied force upon transformation from substrate to products.
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