University of Illinois Urbana-Champaign

Mechanochemical Triggers for Self -Healing Polymers

Hickenboth, Charles Robert

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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
Date of Ingest
2015-09-25T22:13:39Z
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.
Graduation Semester
2006
Type of Resource
text
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http://hdl.handle.net/2142/84247

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