Substituent effects on aggregation phenomena in aqueous solution of thiacarbocyanine dyes

Takahashi, Daisuke; Oda, Hayato; Izumi, Takeshi; Hirohashi, Ryo

doi:10.1016/j.dyepig.2004.08.008

Cited by 36 publications

(46 citation statements)

References 10 publications

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“…The blue-shifted 460 nm peak is characteristic of dimeric H-type aggregate formation and can be associated with the transition to the upper excitonic state of such an H-dimer, [41,44] whereas the 485 nm peak is representative of the non-aggregated dye population. Since the relative intensity of the two bands does not depend on concentration (data not shown), [39] aggregation must be intramolecular: it takes place between the two chromophoric units of the molecule and is strongly favoured by the pre-organisation induced by the linker, which removes the serendipitous diffusion step in dilute solution.…”

Section: Resultsmentioning

confidence: 99%

“…It is known that cyanine dyes undergo aggregation, [44][45][46][47] a phenomenon that is mainly due to a strong hydrophobic effect. Aggregation dramatically changes the photophysical properties of the dyes in solution compared to the monomeric species, in particular the absorption and fluorescence band shape and position ( Figure 2).…”

Section: Resultsmentioning

confidence: 99%

“…Its amplitude follows the trend YOYO-Cl @ YOYOSAC > YOYO-1 @ YOSAC3 @ YOSAC1 % YOSAC2 > YO-PRO-1, confirming that the homodimeric dyes aggregate more efficiently than the monomeric dyes and that, as observed by others, the introduction of a chlorine atom in the 4,4'-position of the benzoxazole ring (YOYO-Cl and YOSAC3) favours aggregation. [44,57] Upon intercalation into DNA, the H-dimers are disrupted, the fluorescence spectra become mirror images of the absorption ( Figure S4 in the Supporting Information) and, as with the homodimeric dyes, the fluorescence intensities and lifetimes increase strongly (Tables 1 and 2; Figure S11 in the Supporting Information).…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

“…The similarity to the spectra obtained with the homodimeric dyes and the position of the aggregate band suggest strongly that the aggregates formed here are dimeric and not higher order H-aggregates. [44] Dimerisation of cyanine dyes is a well-documented phenomenon. [44,45] Higher order aggregates would have an absorption band shifted more to the blue.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

“…[44] Dimerisation of cyanine dyes is a well-documented phenomenon. [44,45] Higher order aggregates would have an absorption band shifted more to the blue. The H-dimer association constant (Table 3) was estimated from the dependence of the absorbance of the monoA C H T U N G T R E N N U N G mer absorption band on the total dye concentration, as suggested by Harris and Hobbs.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

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Structure–Fluorescence Contrast Relationship in Cyanine DNA Intercalators: Toward Rational Dye Design

Fürstenberg

Deligeorgiev

Gadjev

et al. 2007

Chemistry A European J

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The fluorescence enhancement mechanisms of a series of DNA stains of the oxazole yellow (YO) family have been investigated in detail using steady‐state and ultrafast time‐resolved fluorescence spectroscopy. The strong increase in the fluorescence quantum yield of these dyes upon DNA binding is shown to originate from the inhibition of two distinct processes: 1) isomerisation through large‐amplitude motion that non‐radiatively deactivates the excited state within a few picoseconds and 2) formation of weakly emitting H‐dimers. As the H‐dimers are not totally non‐fluorescent, their formation is less efficient than isomerisation as a fluorescent contrast mechanism. The propensity of the dyes to form H‐dimers and thus to reduce their fluorescence contrast upon DNA binding is shown to depend on several of their structural parameters, such as their monomeric (YO) or homodimeric (YOYO) nature, their substitution and their electric charge. Moreover, these parameters also have a substantial influence on the affinity of the dyes for DNA and on the ensuing sensitivity for DNA detection. The results give new insight into the development and optimisation of fluorescent DNA probes with the highest contrast.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Wwwchemeurjorgmentioning

confidence: 99%

Section: Wwwchemeurjorgmentioning

confidence: 99%

Section: Wwwchemeurjorgmentioning

confidence: 99%

See 3 more Smart Citations

Structure–Fluorescence Contrast Relationship in Cyanine DNA Intercalators: Toward Rational Dye Design

Fürstenberg

Deligeorgiev

Gadjev

et al. 2007

Chemistry A European J

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Fluorescence Spectroscopy to Probe Ionic Liquid‐Based Systems

Pandey

Trivedi

Pandey³

2018

Encyclopedia of Analytical Chemistry

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Owing to its inherent sensitivity coupled with multidimensionality, fluorescence spectroscopy has established itself as a versatile tool to investigate complex chemical systems in analytical chemistry. Ionic liquids, for the last couple of decades or so, have emerged as intriguing modern materials in science and technology that display an array of useful and sometimes unconventional features. Steady‐state fluorescence intensity and anisotropy and time‐resolved excited‐state emission intensity and anisotropy decays along with other advanced fluorescence techniques have been employed effectively to analyze, characterize, and explore ionic liquids and ionic liquid‐based systems. The extent of dipolarity afforded by ionic liquids as well as cosolvent/supercritical fluid‐added ionic liquid systems is readily manifested through the response of judiciously selected fluorescence polarity probes. Transient solvation measurements carried out by means of time‐resolved fluorescence measurements are particularly powerful for their ability to parameterize the kinetics of the solvation process within ionic liquids. Dynamic Stokes' shift of appropriate fluorescence probes reveals the presence of several components, thus highlighting the complexity of solvation within ionic liquids and ionic liquid‐based media. Various fluorescence spectroscopic tools are used to establish and characterize macromolecular (surfactant and polymer) and dye aggregation within ionic liquids and ionic liquid‐based media along with aggregation of surface‐active ionic liquids (SAILs) in water.

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Förster Resonance Energy Transfer and Trapping in Selected Systems: Analysis by Monte-Carlo Simulation

Bojarski¹,

Synak²,

Kułak³

et al. 2012

Methods in Molecular Biology

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Substituent effects on aggregation phenomena in aqueous solution of thiacarbocyanine dyes

Cited by 36 publications

References 10 publications

Structure–Fluorescence Contrast Relationship in Cyanine DNA Intercalators: Toward Rational Dye Design

Structure–Fluorescence Contrast Relationship in Cyanine DNA Intercalators: Toward Rational Dye Design

Fluorescence Spectroscopy to Probe Ionic Liquid‐Based Systems

Förster Resonance Energy Transfer and Trapping in Selected Systems: Analysis by Monte-Carlo Simulation

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