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UV-Triggered and Thermo-Induced Crosslinking of Polymers Containing 1-Functionalized Benzocyclobutenes

Abstract Details

2017, Master of Science, University of Akron, Polymer Science.
Benzocyclobutenes (BCBs) and their derivatives have attracted increasing interest due to their stability at room temperature and ability to thermally ring-open to form o-quinodimethanes (o-QDMs) upon heating. o-QDMs are reactive dienes that rapidly react with dienophiles such as maleimides to generate Diels-Alder [4+2] cycloaddition products.1 1-Hydroxy-o-QDM formed upon heating from 1-hydroxyBCB can undergo not only Diels-Alder cycloaddition reactions in the presence of dienophiles, but also rearrange to form o-tolualdehydes in the absence of a dienophile.2 o-Tolualdehydes, however, can isomerize back to 1-hydroxy-o-QDMs when irradiated with UV light.1 UV-triggered Diels-Alder reaction between o-tolualdehyde and a dienophile can be carried out at ambient temperature without an external catalyst, and has been extensively applied to polymer synthesis. 3-6 Nevertheless, previous work focused only on performing this kind of reaction at the polymer chain ends to accomplish either cyclization4 or modular conjugation.6 In addition, thermo-crosslinking of polymers using 1-hydroxyBCBs as crosslinkers have not been reported. This project established appropriate reaction conditions for both thermo-induced Diels-Alder reaction between 1-hydroxyBCB and bismaleimide and UV-triggered Diels-Alder reaction between o-tolualdehyde and bismaleimide. Copolymers of styrene and vinyl-1-acetoxyBCB were prepared via Activator ReGenerated by Electron Transfer Atom Transfer Radical Polymerization (ARGET ATRP). These copolymers underwent transesterification to generate pendant 1-hydroxyBCB moieties. Subsequently, thermo- and photo-induced crosslinking reactions can be conducted on these copolymers.
Coleen Pugh (Advisor)
Li Jia (Committee Member)
72 p.

Recommended Citations

Citations

  • Xing, L. (2017). UV-Triggered and Thermo-Induced Crosslinking of Polymers Containing 1-Functionalized Benzocyclobutenes [Master's thesis, University of Akron]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=akron1491396556917182

    APA Style (7th edition)

  • Xing, Liwen. UV-Triggered and Thermo-Induced Crosslinking of Polymers Containing 1-Functionalized Benzocyclobutenes. 2017. University of Akron, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=akron1491396556917182.

    MLA Style (8th edition)

  • Xing, Liwen. "UV-Triggered and Thermo-Induced Crosslinking of Polymers Containing 1-Functionalized Benzocyclobutenes." Master's thesis, University of Akron, 2017. http://rave.ohiolink.edu/etdc/view?acc_num=akron1491396556917182

    Chicago Manual of Style (17th edition)