Photophysical and aggregation properties of a long-chain squarylium indocyanine dye

Татиколов, А. С.; Costa, Sı́lvia M. B.

doi:10.1016/s1010-6030(01)00405-1

Cited by 42 publications

(31 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This is possibly due to the formation of aggregates, as supported by UV-VIS spectra (vide supra), consistent with quenching processes reported for other SQ dyes [10,11]. Although such low emission from a blank dye sample is preferable to obtain a high signal-to-noise ratio for sensitive detection, the emission intensity for SQ-BA was irreproducible, and decreased over time when the sample solution of the dye was stored in glass or polypropylene wares.…”

Section: Resultssupporting

confidence: 87%

A Long-Wavelength Fluorescent Squarylium Cyanine Dye Possessing Boronic Acid for Sensing Monosaccharides and Glycoproteins with High Enhancement in Aqueous Solution

Saito

Massie

Maeda

et al. 2012

Sensors

View full text Add to dashboard Cite

Fluorescence sensing of saccharides and glycoproteins using a boronic acid functionalized squarylium cyanine dye (“SQ-BA”) is characterized in terms of synthetic, fluorometric, thermodynamic and kinetic parameters. In our previous work, this newly synthesized dye was successfully applied to the separation and quantification of Gram-positive bacteria by capillary electrophoresis with laser-induced fluorescence detection (CE-LIF); however, the fundamental properties of the dye and its saccharide complexes still required elucidation, as presented in this paper. The dye itself forms nonemissive, soluble aggregates in aqueous solution. With the addition of a monosaccharide, the dye aggregate dissociates to form an emissive monomer accompanied by the formation of a cyclic cis-diol ester with long-wavelength emission (λex = 630 nm, λem = 660 nm). A very large fluorescence enhancement factor of 18× was observed for the sensing dye as a fructose complex at pH 10, yielding a limit of detection of 10 μM fructose. The relative order of fluorescence enhancement of SQ-BA with other monosaccharides was found to be: fructose > ribose > arabinose ≈ galactose > xylose > mannose > rhamnose > fucose ≈ glucose; and apparent affinity constants of 102.80, 102.08 and 100.86 M−1 were determined for fructose, ribose and glucose, respectively. Formation of the emissive complexes occurred within minutes, proving the kinetics of the sugar-dye interactions to be suitable for on-column labeling methods in CE-LIF. Furthermore, the sensing dye was successfully applied to glycoproteins, mucin type I–S and type III, which were detected with high sensitivity in batch aqueous solution as a result of the sugar-selective boronic acid-diol esterification as well as hydrophobic interactions.

show abstract

Section: Resultssupporting

confidence: 87%

A Long-Wavelength Fluorescent Squarylium Cyanine Dye Possessing Boronic Acid for Sensing Monosaccharides and Glycoproteins with High Enhancement in Aqueous Solution

Saito

Massie

Maeda

et al. 2012

Sensors

View full text Add to dashboard Cite

show abstract

“…Photophysical properties of dU-SQ in variable DMSO/water concentrations were then studied. Consistent with previous photophysical studies of indolium squaraine dyes, [11,21] for dU-SQ, a linear correlation was observed between the wavelength of absorption maxima and the Bayliss function and Lorentz-Lorenz function, in the nonaggregate domain window, exhibiting solvent-polarity-dependent properties (Supporting Information,Figures S3 and S4). Such solvent-polarity influence, plus the contribution of water-induced H-aggregation, contributed to a 30-fold fluorescence enhancement in DMSO/water mixtures with high DMSO proportions.…”

supporting

confidence: 89%

“…[10] Recently, by studying the photophysical properties of an indolium squaraine dye in different solvent systems, solvent polarity dependent emission was found and the lowest rate constant of nonradiative deactivation (k nr ) was obtained in a viscous alcohol solvent. [11] However, further biological applications may be hindered by poor water solubility.…”

mentioning

confidence: 99%

Deoxyribonucleoside‐Modified Squaraines as Near‐IR Viscosity Sensors

Zhang

Yue

Kim

et al. 2014

Chemistry A European J

View full text Add to dashboard Cite

Deoxyribonucleoside-modified squaraines were synthesized by Sonogashira coupling reactions using an unsymmetrical, terminal alkynylated benzothiazolium squaraine dye. These non-natural nucleosides exhibited fluorescent 'turn-on' properties in viscous conditions with an enhancement of >300-fold. The viscosity-dependent fluorescence enhancement was attributed to a combination of hampering both molecular aggregation and intramolecular bond rotation of the squaraine probe. Fluorescence microscopy allowed visualization of highly viscous regions during various stages of cellular mitosis.

show abstract

“…It occurs through a twisted intramolecular charge transfer (TICT) process that yields a non-radiative decay of the dye excited state, hampering quantitative fast electron injection and consequently limiting the cell efficiency [9]. Different strategies were proposed to block the photoisomerization mechanism in these structures: the doubling of anchoring moieties, the insertion of long alkyl chains on the lateral groups or the functionalization of the squaric core unit [10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Dicyanovinyl and Cyano-Ester Benzoindolenine Squaraine Dyes: The Effect of the Central Functionalization on Dye-Sensitized Solar Cell Performance

et al. 2016

View full text Add to dashboard Cite

Abstract:In order to achieve a greater light absorption in the near-infrared (NIR) region with a panchromatic spectral response and to suppress the photo-isomerisation phenomenon, we herein report the design, synthesis, spectroscopic and electrochemical characterization of novel centrally functionalized symmetric benzoindolenine squaraine dyes. These molecules have shown different photoelectrical conversion properties, depending on the dicyanovinyl and cyano-ester group substitution on the squaric core unit and on the extension of the π-conjugation.

show abstract

Photophysical and aggregation properties of a long-chain squarylium indocyanine dye

Cited by 42 publications

References 40 publications

A Long-Wavelength Fluorescent Squarylium Cyanine Dye Possessing Boronic Acid for Sensing Monosaccharides and Glycoproteins with High Enhancement in Aqueous Solution

A Long-Wavelength Fluorescent Squarylium Cyanine Dye Possessing Boronic Acid for Sensing Monosaccharides and Glycoproteins with High Enhancement in Aqueous Solution

Deoxyribonucleoside‐Modified Squaraines as Near‐IR Viscosity Sensors

Dicyanovinyl and Cyano-Ester Benzoindolenine Squaraine Dyes: The Effect of the Central Functionalization on Dye-Sensitized Solar Cell Performance

Contact Info

Product

Resources

About