Incorporation of Indeno[2,1-c]fluorenes into Polymers via Nucleophilic AromaticSubstitution
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Wright State University / OhioLINK
2017
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| Online Access: | http://rave.ohiolink.edu/etdc/view?acc_num=wright1503673136761061 |
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ndltd-OhioLink-oai-etd.ohiolink.edu-wright15036731367610612021-08-03T07:04:08Z Incorporation of Indeno[2,1-c]fluorenes into Polymers via Nucleophilic AromaticSubstitution Brackett, Nathaniel Chemistry chemistry A difluoro indeno[2,1-c]fluorene monomer was synthesized by a four-stepprocess. The first compound synthesized by a two-step process was 2,5-bis(ethoxycarbonyl)-3,4-di(4-fluorophenyl)cyclopentadienone. The next two compoundssynthesized were diethyl 2,3-bis(fluorophenyl)-5-hexylterephthalate and 2,3-bis(fluorophenyl)-5-hexylterephthalic acid. The final step involved an intramolecularFriedel-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 aseries of nucleophilic aromatic substitution (NAS) polymerization reactions withbisphenol-A in N-methyl-pyrrolidone (NMP) in an attempt to form novel poly(ether etherketone ketone)s containing the indeno[2,1-c]fluorene structure. Analysis of the productby NMR and TLC showed the reaction was unsuccessful and the difluoro monomer didnot undergo significant fluorine displacement. A series of model reactions in NMP anddimethyl sulfoxide (DMSO) also confirmed that the monomer did not undergo fluorinedisplacement 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. 2017-08-29 English text Wright State University / OhioLINK http://rave.ohiolink.edu/etdc/view?acc_num=wright1503673136761061 http://rave.ohiolink.edu/etdc/view?acc_num=wright1503673136761061 unrestricted This thesis or dissertation is protected by copyright: all rights reserved. It may not be copied or redistributed beyond the terms of applicable copyright laws. |
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NDLTD |
| language |
English |
| sources |
NDLTD |
| topic |
Chemistry chemistry |
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Chemistry chemistry Brackett, Nathaniel Incorporation of Indeno[2,1-c]fluorenes into Polymers via Nucleophilic AromaticSubstitution |
| author |
Brackett, Nathaniel |
| author_facet |
Brackett, Nathaniel |
| author_sort |
Brackett, Nathaniel |
| title |
Incorporation of Indeno[2,1-c]fluorenes into Polymers via Nucleophilic AromaticSubstitution |
| title_short |
Incorporation of Indeno[2,1-c]fluorenes into Polymers via Nucleophilic AromaticSubstitution |
| title_full |
Incorporation of Indeno[2,1-c]fluorenes into Polymers via Nucleophilic AromaticSubstitution |
| title_fullStr |
Incorporation of Indeno[2,1-c]fluorenes into Polymers via Nucleophilic AromaticSubstitution |
| title_full_unstemmed |
Incorporation of Indeno[2,1-c]fluorenes into Polymers via Nucleophilic AromaticSubstitution |
| title_sort |
incorporation of indeno[2,1-c]fluorenes into polymers via nucleophilic aromaticsubstitution |
| publisher |
Wright State University / OhioLINK |
| publishDate |
2017 |
| url |
http://rave.ohiolink.edu/etdc/view?acc_num=wright1503673136761061 |
| work_keys_str_mv |
AT brackettnathaniel incorporationofindeno21cfluorenesintopolymersvianucleophilicaromaticsubstitution |
| _version_ |
1719452967963197440 |