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Greene_D_Thesis.pdf (4.69 MB)
ETD Abstract Container
Abstract Header
The Synthesis and Characterization of Double and Triple Tethered Indeno[2.1-c]fluorendiones
Author Info
Greene, Daniel K.
Permalink:
http://rave.ohiolink.edu/etdc/view?acc_num=wright1513941221837164
Abstract Details
Year and Degree
2017, Master of Science (MS), Wright State University, Chemistry.
Abstract
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.
Committee
William Feld, Ph.D. (Advisor)
Eric Fossum, Ph.D. (Committee Member)
Ken Turnbull, Ph.D. (Committee Member)
Pages
66 p.
Subject Headings
Chemistry
Keywords
chemistry
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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)
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Document number:
wright1513941221837164
Download Count:
328
Copyright Info
© 2017, all rights reserved.
This open access ETD is published by Wright State University and OhioLINK.