meso-Substituted bisanthenes as soluble and stable near-infrared dyes

Jinling Li; Kai Zhang; Xiaojie Zhang; Kuo-Wei Huang; Chunyan Chi; Jishan Wu

doi:10.1021/jo902413h

meso-Substituted bisanthenes as soluble and stable near-infrared dyes

Jinling Li, Kai Zhang, Xiaojie Zhang, Kuo-Wei Huang, Chunyan Chi, Jishan Wu

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

69 Citations (SciVal)

Abstract

(Chemical Equation Presented) Three meso-substituted bisanthenes, 4-6, were prepared in a short synthetic route from the bisanthenequinone. They exhibit largely improved stability and solubility in comparison to the parent bisanthene. All of these compounds also show near-infrared (NIR) absorption and emission with high to moderate fluorescence quantum yields. Amphoteric redox behavior was observed for 4-6 by cyclic voltammetry, and these compounds can be reversibly oxidized and reduced into respective cationic and anionic species by both electrochemical and chemical processes. In addition, compound 5 adopts a herringbone π-stacking motif in the single crystal. © 2010 American Chemical Society.

Original language	English (US)
Pages (from-to)	856-863
Number of pages	8
Journal	The Journal of Organic Chemistry
Volume	75
Issue number	3
DOIs	https://doi.org/10.1021/jo902413h
State	Published - Feb 5 2010

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo902413h

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title = "meso-Substituted bisanthenes as soluble and stable near-infrared dyes",

abstract = "(Chemical Equation Presented) Three meso-substituted bisanthenes, 4-6, were prepared in a short synthetic route from the bisanthenequinone. They exhibit largely improved stability and solubility in comparison to the parent bisanthene. All of these compounds also show near-infrared (NIR) absorption and emission with high to moderate fluorescence quantum yields. Amphoteric redox behavior was observed for 4-6 by cyclic voltammetry, and these compounds can be reversibly oxidized and reduced into respective cationic and anionic species by both electrochemical and chemical processes. In addition, compound 5 adopts a herringbone π-stacking motif in the single crystal. {\textcopyright} 2010 American Chemical Society.",

author = "Jinling Li and Kai Zhang and Xiaojie Zhang and Kuo-Wei Huang and Chunyan Chi and Jishan Wu",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was financially supported by the NRF Competitive Research Program (R-143-000-360281) and NUS Young Investigator Award (R-143-000-356101).",

year = "2010",

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day = "5",

doi = "10.1021/jo902413h",

language = "English (US)",

volume = "75",

pages = "856--863",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - meso-Substituted bisanthenes as soluble and stable near-infrared dyes

AU - Li, Jinling

AU - Zhang, Kai

AU - Zhang, Xiaojie

AU - Huang, Kuo-Wei

AU - Chi, Chunyan

AU - Wu, Jishan

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was financially supported by the NRF Competitive Research Program (R-143-000-360281) and NUS Young Investigator Award (R-143-000-356101).

PY - 2010/2/5

Y1 - 2010/2/5

N2 - (Chemical Equation Presented) Three meso-substituted bisanthenes, 4-6, were prepared in a short synthetic route from the bisanthenequinone. They exhibit largely improved stability and solubility in comparison to the parent bisanthene. All of these compounds also show near-infrared (NIR) absorption and emission with high to moderate fluorescence quantum yields. Amphoteric redox behavior was observed for 4-6 by cyclic voltammetry, and these compounds can be reversibly oxidized and reduced into respective cationic and anionic species by both electrochemical and chemical processes. In addition, compound 5 adopts a herringbone π-stacking motif in the single crystal. © 2010 American Chemical Society.

AB - (Chemical Equation Presented) Three meso-substituted bisanthenes, 4-6, were prepared in a short synthetic route from the bisanthenequinone. They exhibit largely improved stability and solubility in comparison to the parent bisanthene. All of these compounds also show near-infrared (NIR) absorption and emission with high to moderate fluorescence quantum yields. Amphoteric redox behavior was observed for 4-6 by cyclic voltammetry, and these compounds can be reversibly oxidized and reduced into respective cationic and anionic species by both electrochemical and chemical processes. In addition, compound 5 adopts a herringbone π-stacking motif in the single crystal. © 2010 American Chemical Society.

UR - http://hdl.handle.net/10754/575536

UR - https://pubs.acs.org/doi/10.1021/jo902413h

UR - http://www.scopus.com/inward/record.url?scp=75749123473&partnerID=8YFLogxK

U2 - 10.1021/jo902413h

DO - 10.1021/jo902413h

M3 - Article

C2 - 20055372

SN - 0022-3263

VL - 75

SP - 856

EP - 863

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 3

ER -

meso-Substituted bisanthenes as soluble and stable near-infrared dyes

Abstract

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CCDC 812853: Experimental Crystal Structure Determination : 7,14-bis(4-(trifluoromethyl)phenyl)phenanthro[1,10,9,8-opqra]perylene

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meso-Substituted bisanthenes as soluble and stable near-infrared dyes

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 812853: Experimental Crystal Structure Determination : 7,14-bis(4-(trifluoromethyl)phenyl)phenanthro[1,10,9,8-opqra]perylene

Cite this