Publication Date

2001

Document Type

Thesis

Committee Members

William Feld (Advisor)

Degree Name

Master of Science (MS)

Abstract

There is a need to functionalize NLO chromophore systems to incorporate them into polymeric matricies by covalent attachment.The functionalization of a series of NLO chromophores based on the N,N-diphenyl-N-[7-(2-benzothiazolyl)-9,9-diethyl-2- fluorenyl ]amine structure has been investigated.All the chromophores were synthesized from the intermediate chromophore N-phenyl-N-[4-(4-bromophenyl)phenyl ]-N-[7-(2- benzothiazolyl)-9,9-diethyl-2-fluorenyl ]amine which was prepared by a six-step process. Bromination of fluorene yielded 2,7-dibromo-fluorene which could be converted to 2,7- dibromo-9,9-diethylfluorene by alkylation with ethyl iodide in DMSO.Reaction of 2,7- dibromo-9,9-diethylfluorene with one equivalent of butyl lithium followed by reaction with DMF provides 2-bromo-7-formyl-9,9-diethylfluorene.Condensation of 2-bromo-7- formyl-9,9-diethylfluorene and 2-aminobenzenethiol in DMSO results in the formation of 7-(2-benzothiazolyl)-2-bromo-9,9-diethylfluorene.The palladium catalyzed reaction of 7- (2-benzothiazolyl)-2-bromo-9,9-diethylfluorene with aniline afforded N-phenyl-N-[7-(2- benzothiazolyl)-9,9-diethyl-2-fluorenyl ]amine which was subjected to a second palladium catalyzed reaction with 4,4 ’-dibromobiphenyl to yield N-phenyl-N-[4-(4- bromophenyl)phenyl ]-N-[7-(2-benzothiazolyl)-9,9-diethyl-2-fluorenyl ]amine.Further reactions have yielded a series of thermally stable NLO chromophores in which the functional group is located in the para position to the amine nitrogen.

Page Count

79

Department or Program

Department of Chemistry

Year Degree Awarded

2001


Included in

Chemistry Commons

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