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Incorporation of Indeno[2,1-c]fluorenes into Polymers via Nucleophilic Aromatic Substitution

Brackett, Nathaniel
http://rave.ohiolink.edu/etdc/view?acc_num=wright1503673136761061

Abstract Details

2017, Master of Science (MS), Wright State University, Chemistry.
A difluoro indeno[2,1-c]fluorene monomer was synthesized by a four-step process. The first compound synthesized by a two-step process was 2,5- bis(ethoxycarbonyl)-3,4-di(4-fluorophenyl)cyclopentadienone. The next two compounds synthesized were diethyl 2,3-bis(fluorophenyl)-5-hexylterephthalate and 2,3- bis(fluorophenyl)-5-hexylterephthalic acid. The final step involved an intramolecular Friedel-Crafts acylation of the terephthalic acid derivative to form 3,10-difluoro-5,8- dioxo-5,8-dihydro-6-hexylindeno[2,1-c]fluorene. The difluoro monomer was reacted in a series of nucleophilic aromatic substitution (NAS) polymerization reactions with bisphenol-A in N-methyl-pyrrolidone (NMP) in an attempt to form novel poly(ether ether ketone ketone)s containing the indeno[2,1-c]fluorene structure. Analysis of the product by NMR and TLC showed the reaction was unsuccessful and the difluoro monomer did not undergo significant fluorine displacement. A series of model reactions in NMP and dimethyl sulfoxide (DMSO) also confirmed that the monomer did not undergo fluorine displacement under polymerization conditions. In addition, the synthesis of diethyl 5,6- diphenyl-2,3-bis(2-thienyl)terephthalate and 2,8-dibromo-5,11-bis(4-bromophenyl)- indeno[1,2-b]fluorene-6,12-dione were carried out.
William Feld, Ph.D. (Advisor)
Eric Fossum, Ph.D. (Committee Member)
Kenneth Turnbull, Ph.D. (Committee Member)
83 p.
Chemistry
chemistry

Recommended Citations

Citations

  • Brackett, N. (2017). Incorporation of Indeno[2,1-c]fluorenes into Polymers via Nucleophilic Aromatic Substitution [Master's thesis, Wright State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=wright1503673136761061

    APA Style (7th edition)

  • Brackett, Nathaniel . Incorporation of Indeno[2,1-c]fluorenes into Polymers via Nucleophilic Aromatic Substitution. 2017. Wright State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=wright1503673136761061.

    MLA Style (8th edition)

  • Brackett, Nathaniel . "Incorporation of Indeno[2,1-c]fluorenes into Polymers via Nucleophilic Aromatic Substitution." Master's thesis, Wright State University, 2017. http://rave.ohiolink.edu/etdc/view?acc_num=wright1503673136761061

    Chicago Manual of Style (17th edition)

wright1503673136761061
428
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This open access ETD is published by Wright State University and OhioLINK.