Far-Red- to NIR-Emitting Adamantyl-Functionalized Squaraine Dye

J-Aggregation, Dissociation, and Cell Imaging

Taihong Liu, Xinglei Liu, Yuanwei Zhang, Mykhailo V. Bondar, Yu Fang, Kevin Belfield

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Squaraine dyes AM-1′ and AM-1 bearing adamantyl termini were synthesized and spectroscopically characterized. AM-1′ exhibited intense absorption and sharp emission in the far-red to near-infrared (NIR) spectral region. The degenerate two-photon absorption (2PA) spectrum of AM-1′ was obtained over a broad spectral range with a maximum cross section of ca. 360 GM. In aqueous solutions, AM-1′ displayed a strong tendency for J-aggregation and the reference AM-1 exhibited entirely different aggregation behavior. We conclude that both the terminal pendant groups and substituents adjacent to the squaraine core play important roles in determining the aggregation behaviors and optical properties of the resultant squaraine dyes. Further an AM-1′/β-cyclodextrin complex dramatically suppressed squaraine π–π stacking and dissociated the J-aggregate. Fluorescence microscopy imaging of HCT 116 cells incubated with the complex was accomplished, suggesting the potential application of this complex in fluorescence bioimaging.

Original languageEnglish (US)
Pages (from-to)4095-4102
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number30
DOIs
StatePublished - Aug 15 2018

Fingerprint

Coloring Agents
Agglomeration
dyes
dissociation
Infrared radiation
Imaging techniques
cells
Bearings (structural)
Fluorescence microscopy
Cyclodextrins
Absorption spectra
Photons
Optical properties
Fluorescence
fluorescence
squaraine
tendencies
aqueous solutions
microscopy
absorption spectra

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Keywords

  • Host–guest systems
  • Imaging agents
  • J-aggregation
  • Photochemistry
  • Squaraine dyes

Cite this

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title = "Far-Red- to NIR-Emitting Adamantyl-Functionalized Squaraine Dye: J-Aggregation, Dissociation, and Cell Imaging",
abstract = "Squaraine dyes AM-1′ and AM-1 bearing adamantyl termini were synthesized and spectroscopically characterized. AM-1′ exhibited intense absorption and sharp emission in the far-red to near-infrared (NIR) spectral region. The degenerate two-photon absorption (2PA) spectrum of AM-1′ was obtained over a broad spectral range with a maximum cross section of ca. 360 GM. In aqueous solutions, AM-1′ displayed a strong tendency for J-aggregation and the reference AM-1 exhibited entirely different aggregation behavior. We conclude that both the terminal pendant groups and substituents adjacent to the squaraine core play important roles in determining the aggregation behaviors and optical properties of the resultant squaraine dyes. Further an AM-1′/β-cyclodextrin complex dramatically suppressed squaraine π–π stacking and dissociated the J-aggregate. Fluorescence microscopy imaging of HCT 116 cells incubated with the complex was accomplished, suggesting the potential application of this complex in fluorescence bioimaging.",
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Far-Red- to NIR-Emitting Adamantyl-Functionalized Squaraine Dye : J-Aggregation, Dissociation, and Cell Imaging. / Liu, Taihong; Liu, Xinglei; Zhang, Yuanwei; Bondar, Mykhailo V.; Fang, Yu; Belfield, Kevin.

In: European Journal of Organic Chemistry, Vol. 2018, No. 30, 15.08.2018, p. 4095-4102.

Research output: Contribution to journalArticle

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AU - Liu, Taihong

AU - Liu, Xinglei

AU - Zhang, Yuanwei

AU - Bondar, Mykhailo V.

AU - Fang, Yu

AU - Belfield, Kevin

PY - 2018/8/15

Y1 - 2018/8/15

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AB - Squaraine dyes AM-1′ and AM-1 bearing adamantyl termini were synthesized and spectroscopically characterized. AM-1′ exhibited intense absorption and sharp emission in the far-red to near-infrared (NIR) spectral region. The degenerate two-photon absorption (2PA) spectrum of AM-1′ was obtained over a broad spectral range with a maximum cross section of ca. 360 GM. In aqueous solutions, AM-1′ displayed a strong tendency for J-aggregation and the reference AM-1 exhibited entirely different aggregation behavior. We conclude that both the terminal pendant groups and substituents adjacent to the squaraine core play important roles in determining the aggregation behaviors and optical properties of the resultant squaraine dyes. Further an AM-1′/β-cyclodextrin complex dramatically suppressed squaraine π–π stacking and dissociated the J-aggregate. Fluorescence microscopy imaging of HCT 116 cells incubated with the complex was accomplished, suggesting the potential application of this complex in fluorescence bioimaging.

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