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The Synthesis and Characterization of Double and Triple Tethered Indeno[2.1-c]fluorendiones

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2017, Master of Science (MS), Wright State University, Chemistry.
A series of terephthalate esters was synthesized via a Diels-Alder reaction between 2,5-dicarboethoxy-3,4-diphenylcyclopentadienone and various alkynes in order to study reaction conditions necessary to synthesize poly(indeno[2,1-c]fluorene-5,8- dione)s. Diethyl 2,3-diphenyl-5-butylterephthalate, 1,4-bis(3,4-diphenyl-2,5-di(ethoxycarbonyl) phenyl)butane and N,N,N-tris(3,4-diphenyl-2,5-di(ethoxycarbonyl)phenylmethyl) amine were synthesized and characterized by IR, 1H NMR, 13C NMR, 13C NMR DEPT135 spectroscopies as well as elemental composition. Hydrolysis conditions of the terephthalates using potassium hydroxide were also investigated. It was found that large stoichiometric equivalents of base coupled with reaction times over twenty-four hours afforded only partially hydrolyzed products. The synthesis of 6-butylindeno[2,1-c]fluoren-5,8-dione was successfully carried out by the sulfuric acid catalyzed, intramolecular, Friedel-Crafts cyclization of 5-butyl- 2,3-diphenyl terephthalic acid. Full spectroscopic, elemental and melting point characterization is reported.
William Feld, Ph.D. (Advisor)
Eric Fossum, Ph.D. (Committee Member)
Ken Turnbull, Ph.D. (Committee Member)
66 p.

Recommended Citations

Citations

  • Greene, D. K. (2017). The Synthesis and Characterization of Double and Triple Tethered Indeno[2.1-c]fluorendiones [Master's thesis, Wright State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=wright1513941221837164

    APA Style (7th edition)

  • Greene, Daniel. The Synthesis and Characterization of Double and Triple Tethered Indeno[2.1-c]fluorendiones. 2017. Wright State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=wright1513941221837164.

    MLA Style (8th edition)

  • Greene, Daniel. "The Synthesis and Characterization of Double and Triple Tethered Indeno[2.1-c]fluorendiones." Master's thesis, Wright State University, 2017. http://rave.ohiolink.edu/etdc/view?acc_num=wright1513941221837164

    Chicago Manual of Style (17th edition)