Issue 31, 2015
From the journal:

Organic & Biomolecular Chemistry

Palladium-catalyzed direct C–H arylations of dioxythiophenes bearing reactive functional groups: a step-economical approach for functional π-conjugated oligoarenes†

Ching-Yuan Liu,‡ab   Hui Chong,‡a   Hsing-An Lin,ac   Yoshiro Yamashita,c   Bin Zhang,d   Kuo-wei Huang,d   Daizuke Hashizumee  and  Hsiao-hua Yu*af  

* Corresponding authors

a Responsive Organic Materials Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
E-mail: bruceyu@gate.sinica.edu.tw
Tel: +886-2-2789-8634

b Department of Chemical and Material Engineering, National Central University, Jhongli City, Taoyuan 32001, Taiwan

c Department of Electronic Chemistry, Interdisciplinary Graduate School of Science and Engineering, Tokyo Institute of Technology, Japan

d KAUST Catalysis Center and Division of Physical Sciences and Engineering, King Abdullah University of Science and Technology, Thuwal 23955-6900, Saudi Arabia

e Materials Characterization Support Unit, RIKEN Center for Emergent Matter Science, Japan

f Institute of Chemistry, Academia Sinica, 128 Academic Road, Sec. 2, Nankang, Taipei 11529, Taiwan

Abstract

A Pd-catalyzed single-step C–H arylation of dioxythiophene derivatives 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) and environmentally friendly (no toxic metal-containing by-products) and the oligoarenes synthesized are potentially applicable for bio-labeling, bioimaging, and biosensing.

Graphical abstract: Palladium-catalyzed direct C–H arylations of dioxythiophenes bearing reactive functional groups: a step-economical approach for functional π-conjugated oligoarenes

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Article information

DOI
https://doi.org/10.1039/C5OB00705D
Article type
Paper
Submitted
08 Apr 2015
Accepted
25 Jun 2015
First published
25 Jun 2015

Org. Biomol. Chem., 2015,13, 8505-8511

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Palladium-catalyzed direct C–H arylations of dioxythiophenes bearing reactive functional groups: a step-economical approach for functional π-conjugated oligoarenes

C. Liu, H. Chong, H. Lin, Y. Yamashita, B. Zhang, K. Huang, D. Hashizume and H. Yu, Org. Biomol. Chem., 2015, 13, 8505 DOI: 10.1039/C5OB00705D

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