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

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 Zheng, Kuo-Wei Huang, Daisuke Hashizume, Hsiao-hua Yu

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

7 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 language	English (US)
Pages (from-to)	8505-8511
Number of pages	7
Journal	Org. Biomol. Chem.
Volume	13
Issue number	31
DOIs	https://doi.org/10.1039/C5OB00705D
State	Published - 2015

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10.1039/C5OB00705D

https://repository.kaust.edu.sa/bitstream/10754/558679/1/C5OB00705D.pdf

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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 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.",

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

note = "KAUST Repository Item: Exported on 2020-10-01",

year = "2015",

doi = "10.1039/C5OB00705D",

language = "English (US)",

volume = "13",

pages = "8505--8511",

journal = "Org. Biomol. Chem.",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

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T1 - Palladium-Catalyzed Direct C-H Arylations of Dioxythiophenes Bearing Reactive Functional Groups: A Step-Economical Approach for Functional π-Conjugated Oligoarenes

AU - Liu, Ching-Yuan

AU - Chong, Hui

AU - Lin, Hsing-An

AU - Yamashita, Yoshiro

AU - Zheng, Bin

AU - Huang, Kuo-Wei

AU - Hashizume, Daisuke

AU - Yu, Hsiao-hua

N1 - KAUST Repository Item: Exported on 2020-10-01

PY - 2015

Y1 - 2015

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/558679

UR - http://pubs.rsc.org/en/Content/ArticleLanding/2015/OB/C5OB00705D

UR - http://www.scopus.com/inward/record.url?scp=84938386495&partnerID=8YFLogxK

U2 - 10.1039/C5OB00705D

DO - 10.1039/C5OB00705D

M3 - Article

SN - 1477-0520

VL - 13

SP - 8505

EP - 8511

JO - Org. Biomol. Chem.

JF - Org. Biomol. Chem.

IS - 31

ER -

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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CCDC 1055681: Experimental Crystal Structure Determination : ((5,7-bis(4'-propylbiphenyl-4-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methoxy)acetic acid

CCDC 1055679: Experimental Crystal Structure Determination : (5,7-bis(4'-propylbiphenyl-4-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methanol

CCDC 1055680: Experimental Crystal Structure Determination : 1,1'-((2-(hydroxymethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-diyl)di-4,1-phenylene)diethanone

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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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CCDC 1055681: Experimental Crystal Structure Determination : ((5,7-bis(4'-propylbiphenyl-4-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methoxy)acetic acid

CCDC 1055679: Experimental Crystal Structure Determination : (5,7-bis(4'-propylbiphenyl-4-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methanol

CCDC 1055680: Experimental Crystal Structure Determination : 1,1'-((2-(hydroxymethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-diyl)di-4,1-phenylene)diethanone

Cite this