Synthesis and characterization of molecules for electron transfer research.

Description:

Dimethoxynaphthalene (donor) and quinone (acceptor) have been chosen as a suitable redox pair and are bonded to either permethylated silane chains or corresponding permethylated alkyl chains to form Acceptor-(Bridge)-Donor molecules. The idea that the s-delocalization phenomenon of silane chains may greatly facilitate ET reactions will be tested. The starting material for the donor precursor, 4-(1,4-dimethoxynaphthyl)bromocyclohexane, was 1,4-naphthoquinone. After methylation and bromination, the Grignard reagent of the resulting bromide was reacted with cyclohexanedione, mono ethylene ketal. The resulting alcohol was changed to the donor precursor through the following functional group transformation steps: dehydration, hydrogenation, deketalization and bromination. 1,4-Dibenzyloxybromobenzene, the precursor for the acceptor, was synthesized from 1,4-hydroquinone through bromination and benzylation. The connection of the two precursors and either permethylated silane chains or permethylated alkyl chains will give the final target molecules for ET research. Progress on this is included.

Creator(s): Xiao, Wu
Creation Date: December 2000
Partner(s):
UNT Libraries
Collection(s):
UNT Theses and Dissertations
Usage:
Total Uses: 278
Past 30 days: 3
Yesterday: 0
Creator (Author):
Publisher Info:
Publisher Name: University of North Texas
Place of Publication: Denton, Texas
Date(s):
  • Creation: December 2000
  • Digitized: August 2, 2007
Description:

Dimethoxynaphthalene (donor) and quinone (acceptor) have been chosen as a suitable redox pair and are bonded to either permethylated silane chains or corresponding permethylated alkyl chains to form Acceptor-(Bridge)-Donor molecules. The idea that the s-delocalization phenomenon of silane chains may greatly facilitate ET reactions will be tested. The starting material for the donor precursor, 4-(1,4-dimethoxynaphthyl)bromocyclohexane, was 1,4-naphthoquinone. After methylation and bromination, the Grignard reagent of the resulting bromide was reacted with cyclohexanedione, mono ethylene ketal. The resulting alcohol was changed to the donor precursor through the following functional group transformation steps: dehydration, hydrogenation, deketalization and bromination. 1,4-Dibenzyloxybromobenzene, the precursor for the acceptor, was synthesized from 1,4-hydroquinone through bromination and benzylation. The connection of the two precursors and either permethylated silane chains or permethylated alkyl chains will give the final target molecules for ET research. Progress on this is included.

Degree:
Level: Master's
Discipline: Chemistry
Language(s):
Subject(s):
Keyword(s): Coupling reactions | chromatography | electron transfer
Contributor(s):
Partner:
UNT Libraries
Collection:
UNT Theses and Dissertations
Identifier:
  • OCLC: 50567148 |
  • ARK: ark:/67531/metadc2683
Resource Type: Thesis or Dissertation
Format: Text
Rights:
Access: Public
License: Copyright
Holder: Xiao, Wu
Statement: Copyright is held by the author, unless otherwise noted. All rights reserved.