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Preparation of cellulose derivatives containing carbazole chromophore

✍ Scribed by Lijun Mao; Anna M. Ritcey


Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
174 KB
Volume
74
Category
Article
ISSN
0021-8995

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✦ Synopsis


Cellulose derivatives containing long hydrocarbon side chains and the carbazole chromophore are prepared. N-4Ј-Bromobutylcarbazole is first synthesized from carbazole and 1,4-dibromobutane. Alkylated carbazole is then reacted with cellulose acetate in dimethyl sulfoxide solution to produce cellulose ethers containing the desired chromophore. Polymers containing a mixture of alkyl side chains are also prepared by the subsequent addition of 1-bromododecane to the reaction mixture. Characterization of the resulting cellulose derivatives by FTIR spectroscopy indicates that the deacetylation of cellulose acetate and the subsequent etherification are both complete. In addition, the incorporation of the carbazole chromophore is clearly shown by 1 H-and 13 C-NMR spectroscopy. Polymers of different carbazole content, ranging from 2.9 to 1.1 chromophores per anhydroglucose repeat unit, are obtained by varying the reaction conditions. Substitution is found to be controlled primarily by the quantity of alkylating agent introduced while variation of the reaction time has little effect. This method is used to prepare (dodecyl) y (N-4Ј-carbazolylbutyl) x cellulose, (decyl) y (N-4Ј-carbazolylbutyl) x cellulose, and (butyl) y (N-4Ј-carbazolylbutyl) x cellulose. Cellulose acetate can be replaced by (methyl)cellulose as the starting material to obtain analogous products.


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