Effect of fluorination of 2,1,3-benzothiadiazole
Christian B Nielsen1, Andrew J P White1, Iain McCulloch1,2
1†Department of Chemistry and Centre for Plastic Electronics, Imperial College London, London SW7 2AZ, United Kingdom.
Abstract:
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.
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Reactions at the Benzylic Position: Halogenation
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Variables Affecting Phosphorescence and Fluorescence
Electrophilic Aromatic Substitution: Sulfonation of Benzene


