Effect of Fluorination of 2,1,3-Benzothiadiazole

The 4,7-dithieno-2,1,3-benzothiadiazole (DTBT) moiety and its fluorinated counterpart are important π-conjugated building blocks in the field of organic electronics. Here we present a combined experimental and theoretical investigation into fundamental properties relating to these two molecular enti...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-05, Vol.80 (10), p.5045-5048
Main Authors: Nielsen, Christian B, White, Andrew J. P, McCulloch, Iain
Format: Article
Language:English
Subjects:
absorption
electronics
moieties
organic chemistry
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Summary:The 4,7-dithieno-2,1,3-benzothiadiazole (DTBT) moiety and its fluorinated counterpart are important π-conjugated building blocks in the field of organic electronics. Here we present a combined experimental and theoretical investigation into fundamental properties relating to these two molecular entities and discuss the potential impact on extended π-conjugated materials and their electronic properties. While the fluorinated derivative, in the solid state, packs with a cofacial overlap smaller than that of DTBT, we report experimental evidence of stronger optical absorption as well as stronger intra- and intermolecular contacts upon fluorination.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.5b00430