Palladium-Catalyzed Direct C-H Arylations of Dioxythiophenes Bearing Reactive Functional Groups: A Step-Economical Approach for Functional π-Conjugated Oligoarenes

A Pd-catalyzed and single-step C-H arylation of dioxythiophene derivates bearing unprotected reactive functional groups (-OH, -COOH, -N3) in a phosphine-free manner has been developed. Various dioxythiopene-based oligoarenes with extended π-conjugation are obtained with good yields (up to 90%). These oligoarenes display suitable optical properties (absorption and emission maxima, quantum yields) and contain reactive functional groups suitable for further conjugations with bioactive molecules. This new methodology is step economical (fewer synthetic steps), environmental friendly (no toxic metal-containing side-poducts) and the oligoarenes synthesized are potentially applicable for bio-labeling, bioimaging, and biosensing.

Citation

Palladium-Catalyzed Direct C-H Arylations of Dioxythiophenes Bearing Reactive Functional Groups: A Step-Economical Approach for Functional π-Conjugated Oligoarenes 2015 Org. Biomol. Chem.

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[Dataset]
Liu, C.-Y., Chong, H., Lin, H.-A., Yamashita, Y., Zhang, B., Huang, K.-W., … Yu, H.-H. (2015). CCDC 1055679: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc14fj58. DOI: 10.5517/cc14fj58 HANDLE: 10754/624421
[Dataset]
Liu, C.-Y., Chong, H., Lin, H.-A., Yamashita, Y., Zhang, B., Huang, K.-W., … Yu, H.-H. (2015). CCDC 1055680: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc14fj69. DOI: 10.5517/cc14fj69 HANDLE: 10754/624422
[Dataset]
Liu, C.-Y., Chong, H., Lin, H.-A., Yamashita, Y., Zhang, B., Huang, K.-W., … Yu, H.-H. (2015). CCDC 1055681: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc14fj7b. DOI: 10.5517/cc14fj7b HANDLE: 10754/624423

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Nanofabrication Core Lab; Articles; Analytical Chemistry Core Lab; Imaging and Characterization Core Lab; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)