Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Comparison of Photocyclization Reactions of Fluoro- vs Nonfluoro-Substituted Polymethyleneoxy Donor Linked Phthalimides

  • Park, Hea Jung (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Ryu, Young Ju (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Kim, Kyung Mok (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Yoon, Ung Chan (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Kim, Eunae (BK-21 Project Team, College of Pharmacy, Chosun University) ;
  • Sohn, Youngku (Department of Chemistry, Yeungnam University) ;
  • Cho, Dae Won (Department of Chemistry, Yeungnam University) ;
  • Mariano, Patrick S. (Department of Chemistry and Chemical Biology, University of New Mexico)
  • Received : 2012.12.19
  • Accepted : 2013.01.14
  • Published : 2013.04.20
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Abstract

Photochemical reactions of fluoro- vs. nonfluoro-substituted polymethylenoxy chain linked phthalimide were carried out to explore how electronegative fluorine atoms inside the donor chain influence photocyclization reaction efficiencies and to briefly determine the alkali metal binding properties of the photoproducts. The results of this study show that the fluorine-substituted donor chain linked phthalimide undergoes inefficient photocyclization via single electron transfer (SET)-induced excited state pathways to generate 14-membered cyclic amidol compared to nonfluoro-analog due to low electron donor ability of the terminal oxygen donor site. These results show that photoinduced intramolecular SET processes arising from ${\alpha}$-silyl ether electron donors to phthalimides are largely dependent on the kinds of substituents inside donor chain. Finally, a preliminary study with the cyclic amidols generated in this effort showed that they have weak alkali metal cation binding properties regardless of absence/presence of fluoro-substituents.

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References

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