The Functionalization of Thermally Stable Third-Order NLO Chromophores

 
 
 
 

The Functionalization of Thermally Stable Third-Order NLO Chromophores

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Title: The Functionalization of Thermally Stable Third-Order NLO Chromophores
Author: Sawyer, James Richard
Description: Sawyer,James R. M.S.,Department of Chemistry,Wright State University,2001. The Functionalization of Thermally Stable Third-Order NLO Chromophores. 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.
Permanent Link: http://rave.ohiolink.edu/etdc/view?acc_num=wright1033149434
http://hdl.handle.net/2374.OX/19607
Date: 2001

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