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

Ching-Yuan Liu, Hui Chong, Hsing-An Lin, Yoshiro Yamashita, Bin Zheng, Kuo-Wei Huang, Daisuke Hashizume, Hsiao-hua Yu

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

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.
Original languageEnglish (US)
Pages (from-to)8505-8511
Number of pages7
JournalOrg. Biomol. Chem.
Volume13
Issue number31
DOIs
StatePublished - 2015

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