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 Zhang; Kuo Wei Huang; Daizuke Hashizume; Hsiao Hua Yu

doi:10.1039/c5ob00705d

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 Zhang, Kuo Wei Huang, Daizuke Hashizume, Hsiao Hua Yu

Department of Chemical and Materials Engineering

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

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.

Original language	English
Pages (from-to)	8505-8511
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	13
Issue number	31
DOIs	https://doi.org/10.1039/c5ob00705d
State	Published - 21 Aug 2015

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10.1039/c5ob00705d

CCDC 1055681: Experimental Crystal Structure Determination
Liu, C.-Y. (Creator), Chong, H. (Creator), Lin, H.-A. (Creator), Yamashita, Y. (Creator), Zhang, B. (Creator), Huang, K.-W. (Creator), Hashizume, D. (Creator) & Yu, H.-H. (Creator), The Cambridge Structural Database, 2015
DOI: 10.5517/cc14fj7b, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc14fj7b&sid=DataCite
Dataset
CCDC 1055680: Experimental Crystal Structure Determination
Liu, C.-Y. (Creator), Chong, H. (Creator), Lin, H.-A. (Creator), Yamashita, Y. (Creator), Zhang, B. (Creator), Huang, K.-W. (Creator), Hashizume, D. (Creator) & Yu, H.-H. (Creator), The Cambridge Structural Database, 2015
DOI: 10.5517/cc14fj69, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc14fj69&sid=DataCite
Dataset
CCDC 1055679: Experimental Crystal Structure Determination
Liu, C.-Y. (Creator), Chong, H. (Creator), Lin, H.-A. (Creator), Yamashita, Y. (Creator), Zhang, B. (Creator), Huang, K.-W. (Creator), Hashizume, D. (Creator) & Yu, H.-H. (Creator), The Cambridge Structural Database, 2015
DOI: 10.5517/cc14fj58, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc14fj58&sid=DataCite
Dataset

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title = "Palladium-catalyzed direct C-H arylations of dioxythiophenes bearing reactive functional groups: A step-economical approach for functional π-conjugated oligoarenes",

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.",

author = "Liu, {Ching Yuan} and Hui Chong and Lin, {Hsing An} and Yoshiro Yamashita and Bin Zhang and Huang, {Kuo Wei} and Daizuke Hashizume and Yu, {Hsiao Hua}",

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T1 - Palladium-catalyzed direct C-H arylations of dioxythiophenes bearing reactive functional groups

T2 - A step-economical approach for functional π-conjugated oligoarenes

AU - Liu, Ching Yuan

AU - Chong, Hui

AU - Lin, Hsing An

AU - Yamashita, Yoshiro

AU - Zhang, Bin

AU - Huang, Kuo Wei

AU - Hashizume, Daizuke

AU - Yu, Hsiao Hua

PY - 2015/8/21

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N2 - 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.

AB - 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.

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U2 - 10.1039/c5ob00705d

DO - 10.1039/c5ob00705d

M3 - 期刊論文

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EP - 8511

JO - Organic and Biomolecular Chemistry

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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

Abstract

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Datasets

CCDC 1055681: Experimental Crystal Structure Determination

CCDC 1055680: Experimental Crystal Structure Determination

CCDC 1055679: Experimental Crystal Structure Determination

Cite this