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 D.

doi:10.1002/ejoc.201800584

Cited by 18 publications

(12 citation statements)

References 75 publications

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“…On the basis of cell viability test results, 30 μM squaraine 1 and 10 μM squaraine 2 in solution were used for fluorescence cell imaging for the HeLa cell line. , As presented in Figure , cells incubated with compound 1 exhibited bright fluorescence in the cytoplasm area. In comparison, dye accumulation surrounding the nucleus area was observed for cells incubated with squaraine 2 (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Electronic Nature of Neutral and Charged Two-Photon Absorbing Squaraines for Fluorescence Bioimaging Application

et al. 2019

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The electronic properties of neutral 2,4-bis(4-bis(2-hydroxyethyl) amino-2-hydroxy-6-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)phenyl)squaraine (1) and charged 2-((3-octadecylbenzothiazol-2(3H)-ylidene)methyl)-3-oxo-4-((3-(4-(pyridinium-1-yl)butyl)benzo-thiazol-3-ium-2-yl)methylene)cyclobut-1-enolate iodide (2) squaraine derivatives were analyzed based on comprehensive linear photophysical, photochemical, nonlinear optical studies (including two-photon absorption (2PA) and femtosecond transient absorption spectroscopy measurements), and quantum chemical calculations. The steady-state absorption, fluorescence, and excitation anisotropy spectra of these new squaraines revealed the values and mutual orientations of the main transition dipoles of 1 and 2 in solvents of different polarity, while their role in specific nonlinear optical properties was shown. The degenerate 2PA spectra of 1 and 2 exhibited similar shapes, with maximum cross sections of ∼300–400 GM, which were determined by the open aperture Z-scan method over a broad spectral range. The nature of the time-resolved excited-state absorption spectra of 1 and 2 was analyzed using a femtosecond transient absorption pump–probe technique and the characteristic relaxation times of 4–5 ps were revealed. Quantum chemical analyses of the electronic properties of 1 and 2 were performed using the ZINDO/S//DFT theory level, affording good agreement with experimental data. To demonstrate the potential of squaraines 1 and 2 as fluorescent probes for bioimaging, laser scanning fluorescence microscopy images of HeLa cells incubated with new squaraines were obtained.

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Section: Resultsmentioning

confidence: 99%

Electronic Nature of Neutral and Charged Two-Photon Absorbing Squaraines for Fluorescence Bioimaging Application

et al. 2019

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“…[14] Red-emitting AIEgens are known to be important for in vivo as well as in vitro bio-imaging of cells. [15,16] They are also well-known for their bio-medical applications such as antioxidant, antidiabetic, anti-inflammatory, anti-microbial, anti-viral, and anti-cancer etc. [17][18][19][20][21][22] Incorporation of branched conjugation to the strong electron-rich center can increase the extent of electronic communication between donor (D) and acceptor (A) in a crossconjugated system and thus can display interesting photophysical properties.…”

Section: Introductionmentioning

confidence: 99%

Multi Stimuli Responsive Non‐Doped Red Emitting AIEE Active Phenothiazine‐Based Chalcones: Crystal Structure, Solvatochromism, Turn‐on Mechanofluorochromism and Acidochromism

Kumari

Milton

2022

Eur J Org Chem

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We report on a series of phenothiazine‐based D‐π‐A‐π‐D type cross‐conjugated non‐doped red‐emitting molecules synthesized by simple Claisen‐Schmidt condensation, which exhibit excellent AIEE phenomena through the formation of large‐sized nano‐aggregates. These thermally stable red fluorescent organic materials have low band gap energies (Eg=1.84–2.15 eV) and also display reversible mechanofluorochromism. The CIE chromaticity coordinates of red emissive ground powders were closer to the standard red‐light chromaticity coordinates. These chalcones also exhibited positive solvatochromism, and large Stokes shifts. Finally, these compounds were utilized as reversible volatile acid sensors to detect TFA in solution as well as in solid state, by virtue of the presence of electron withdrawing carbonyl oxygen, and they could detect TFA at a concentration as low as 15.8 ppm in the presence of C4.

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“…Squaraine (SQ), a class of dyes having sharp and intense absorption and fluorescence in near-infrared region, have been used as sensors for ions, and exploited in biomedical imaging. − In aqueous solution, squaraine dyes favor to form an aggregate assembly of H-aggregates (chromophores in a parallel-oriented fashion) or J-aggregates (arrangement in a head-to-tail arrangement) through intermolecular π–π and hydrophobic interactions . Correspondingly, the fluorescence of SQ is very weak because of aggregation quenching property.…”

Section: Introductionmentioning

confidence: 99%

Media Dependent Switching of Selectivity and Continuous near Infrared Turn-on Fluorescence Response through Cascade Interactions from Noncovalent to Covalent Binding for Detection of Serum Albumin in Living Cells

Zheng

Sun

et al. 2018

ACS Appl. Mater. Interfaces

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Abnormal level of proteins is proved to be associated with diseases. Thus, protein sensing is helpful for clinical diagnosis and therapy. However, there is a great variety of protein species and relatively low concentration of each protein in complicated biological systems including other nonprotein biomolecules. Therefore, it remains challenging to develop an effective method for detecting protein with high selectivity and sensitivity. Herein, a new self-assembly method based on a robust dye SQSS of which two squaraine molecules were conjugated through disulfide bond was developed for highly selective and sensitive detection of serum albumin (SA) in aqueous solution and live cells. SQSS can self-assemble into "compact" aggregates, offering "inert" disulfide group and very low background fluorescence through the combination of aggregation quenching and homogeneous fluorescence resonance energy transfer (homoFRET) quenching. The response of SQSS to SA undergoes two cascade stages. At the first stage, SA drives the compact assemblies of SQSS to form loose ones with fast speed (30 s) through noncovalent interaction, resulting in the enhancement of fluorescence to some extent. In this loose assembly state, the disulfide bond in SQSS is reactive. At the second stage, the Cys34 in SA slowly induced further disassembly through covalent binding with reactive disulfide bond, resulting in fluorescence further increasing and SQSS labeling to SA that cannot be displaced by site binding ligands of SA. The self-assemblies of SQSS can selectively detect SA with continuous near-infrared (NIR) turn-on fluorescence response in 100% aqueous buffer solution. In addition, SQSS showed the potential application of imaging SA in living cells. On the other hand, the loose assembly state of SQSS was also achieved in aqueous solution with 20% CH 3 CN. In this media, thiol-containing glutathione (GSH) caused the disassembly of SQSS with turn-on fluorescence response through interaction with disulfide bond. SQSS can selectively recognize GSH over other amino acids even in the presence of other sulfhydryl amino acids. As a proof-of-concept method, the molecular self-assembly through multisteps interactions would provide an ideal strategy for detection and live-cell imaging of biorelated molecules with high selectivity and signal-to-noise ratio.

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Far‐Red‐ to NIR‐Emitting Adamantyl‐Functionalized Squaraine Dye: J‐Aggregation, Dissociation, and Cell Imaging

Cited by 18 publications

References 75 publications

Electronic Nature of Neutral and Charged Two-Photon Absorbing Squaraines for Fluorescence Bioimaging Application

Electronic Nature of Neutral and Charged Two-Photon Absorbing Squaraines for Fluorescence Bioimaging Application

Multi Stimuli Responsive Non‐Doped Red Emitting AIEE Active Phenothiazine‐Based Chalcones: Crystal Structure, Solvatochromism, Turn‐on Mechanofluorochromism and Acidochromism

Media Dependent Switching of Selectivity and Continuous near Infrared Turn-on Fluorescence Response through Cascade Interactions from Noncovalent to Covalent Binding for Detection of Serum Albumin in Living Cells

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