Novel Highly Fluorescent Triphenylamine-Based Oligothiophenes

A homologous series of novel amorphous oligothienyl-triphenylamines, comprised of head-to-tail coupled oligo(3-hexylthiophene)s covalently linked to a triphenylamine core, are disclosed. These hybrid systems, which differ by the length of the oligothiophene units from a monothiophene up to a quatert...

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Bibliographic Details
Published in:Chemistry of materials 2007-08, Vol.19 (17), p.4155-4165
Main Authors: Cremer, Jens, Briehn, Christoph A
Format: Article
Language:English
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Summary:A homologous series of novel amorphous oligothienyl-triphenylamines, comprised of head-to-tail coupled oligo(3-hexylthiophene)s covalently linked to a triphenylamine core, are disclosed. These hybrid systems, which differ by the length of the oligothiophene units from a monothiophene up to a quaterthiophene, were created via palladium-catalyzed cross-coupling reactions in good yields. The optical and electrochemical properties of these compounds were thoroughly investigated and are compared to the corresponding parent linear non-functionalized oligothiophenes, clearly demonstrating that these newly synthesized hybrid systems are characterized by outstanding absorption and emission properties. These molecules exhibit fluorescence quantum yields as high as 65%, which is unexpectedly high for thiophene-based materials. Based on this available data set, structure−property relationships were established, providing a deeper insight into the electronic nature of these materials and in this respect elucidating electronic differences between these star-shaped structures and their corresponding parent linear oligothiophenes.
ISSN:0897-4756
1520-5002
DOI:10.1021/cm0700448