Organic semiconductors are promising as building blocks for the next generation electronic devices due to their properties such as low cost, flexibility and comparability with plastics. Recently, a large number of tetracene and pentacene derivatives have been synthesized and reported as high performance organic semiconductors. One synthetic pathway towards tetracene derivatives is Friedel Crafts acylation reaction. In this thesis, the synthesis of 6,11-dihydroxy naphthacene-5,12-dione was investigated, and reaction condition was optimized. The experiments show that washing steps have great impact on the quality of the product, and the sequence of adding reactants is crucial to the synthesis. The best solvent for the synthesis is nitrobenzene. In the second part of this thesis the synthesis of some anthracene derivatives was exploited. With sodium dithionate, 1,4-dimethoxyl antracene-9,10-dione can be reduced to the desired product R4(dihydroxyl dimethoxyl anthracene), but 1,4-hydroxy anthracene-9,10-dione is reduced to R2, a tautomer of the expected compound R1. Using NaBH4as the reducing reagent, an unexpected anthracene derivative is obtained, where the two oxygen atoms are removed from the structure and the molecule is fully conjugated.
Language
eng
File Type
pdf
File Size
2759549 bytes
Date Available
January 12, 2018
LC Number
T378.24 T833a
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