Effect of fluorination of 2, 1, 3-benzothiadiazole

C.B. Nielsen, A.J.P. White, I. McCulloch
J. Org. Chem., 80 (10), 5045-5048, (2015)

Effect of fluorination of 2, 1, 3-benzothiadiazole


2,1,3-benzothiadiazole (DTBT), -conjugated


​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.


DOI: 10.1021/acs.joc.5b00430


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