The effect of anionic, cationic and neutral surfactants on the photophysics and isomerization of 3,3′-diethylthiacarbocyanine

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

doi:10.1039/b104807b

Cited by 23 publications

(33 citation statements)

References 44 publications

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“…While trans-cis (photo)isomerization of various compounds is widely used in molecular photoswitches, over the past decades, most works have been focused mainly on azobenzene derivatives [63], spiropyrans [64], diarylethenes [65], and stilbenes [66], and, until recently, this property of cyanine dyes has not been applied in practice. The use of cyanine photoisomerization in research is mainly for probing microviscosity of microheterogeneous media [67,68]. On the contrary, rigidization of the polymethine chain of dyes is often carried out by introducing "bridges" that suppress internal conversion and photoisomerization processes to increase the stability of the dyes and the fluorescence quantum yield [17,18,69,70].…”

Section: Isomerization Of Cyanine Dyes In Structurally Organized Mediamentioning

confidence: 99%

Isomerization and Properties of Isomers of Carbocyanine Dyes

Пронкин

Татиколов

2019

Sci

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One of the important features of polymethine (cyanine) dyes is isomerization about one of C–C bonds of the polymethine chain. In this review, spectral properties of the isomers, photoisomer-ization and thermal back isomerization of carbocyanine dyes, mostly meso-substituted carbocy-anine dyes, are considered. meso-Alkyl-substituted thiacarbocyanine dyes are present in polar solvents mainly as cis isomers and, hence, exhibit no photoisomerization, whereas in nonpolar solvents, in which the dyes are in the trans form, photoisomerization takes place. In contrast, the meso-substituted dyes 3,3′-dimethyl-9-phenylthiacarbocyanine and 3,3′-diethyl-9-(2-hydroxy-4-methoxyphenyl)thiacarbocyanine occur as trans isomers and exhibit photoisomerization in both polar and nonpolar solvents. The behavior of these dyes may be ex-plained by the fact that the phenyl ring of the substituent in their molecules can be twisted at some angle, removing the substituent from the plane of the molecule and reducing its steric ef-fect on the conformation of the trans isomer. In some cases, photoisomerization of cis isomers of meso-substituted carbocyanine dyes is also observed (for some meso-alkyl-substituted dyes com-plexed with DNA and chondroitin-4-sulfate; for 3,3′-diethyl-9-methoxythiacarbocyanine in moderate polarity solvents). The cycle photoisomerization–thermal back isomerization of cya-nine dyes can be used in various systems of information storage and deserves further investiga-tion using modern research methods.

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Section: Isomerization Of Cyanine Dyes In Structurally Organized Mediamentioning

confidence: 99%

Isomerization and Properties of Isomers of Carbocyanine Dyes

Пронкин

Татиколов

2019

Sci

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“…DiD‐loaded QSs with DID loadings, L = moles DID /(moles CTAB + moles Cholesterol ), ranging from 0.6 × 10 −3 to 6.6 × 10 −3 (Table S1, Supporting Information) were prepared using the DELOS‐SUSP methodology . The physicochemical properties of the resulting vesicles with L = 1.3 × 10 −3 (D‐QS‐2) are here compared with those of other DiD‐loaded QSs obtained by other methods generally used for the preparation of loaded vesicles, such as incubation (D‐QS‐2‐IC), sonication (D‐QS‐2‐SON), and thin‐film hydration (D‐QS‐2‐TFH) . The normalized UV–vis absorption spectra of DiD‐loaded QSs prepared by different routes are shown in Figure for comparison along with the spectra of solvated DiD in ethanol (EtOH) and nanoparticles of pure DiD (D‐NP) in water, obtained by the DELOS‐SUSP method but without using the surfactant (see the Supporting Information).…”

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confidence: 99%

Nanostructuring Lipophilic Dyes in Water Using Stable Vesicles, Quatsomes, as Scaffolds and Their Use as Probes for Bioimaging

Ardizzone

Illa-Tuset

Faraudo

et al. 2018

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A new kind of fluorescent organic nanoparticles (FONs) is obtained using quatsomes (QSs), a family of nanovesicles proposed as scaffolds for the nanostructuration of commercial lipophilic carbocyanines (1,1'-dioctadecyl-3,3,3',3'-tetramethyl-indocarbocyanine perchlorate (DiI), 1,1'-dioctadecyl-3,3,3',3'-tetramethyl-indodicarbocyanine perchlorate (DiD), and 1,1'-dioctadecyl-3,3,3',3'-tetramethyl-indotricarbocyanine iodide (DiR)) in aqueous media. The obtained FONs, prepared by a CO -based technology, show excellent colloidal- and photostability, outperforming other nanoformulations of the dyes, and improve the optical properties of the fluorophores in water. Molecular dynamics simulations provide an atomistic picture of the disposition of the dyes within the membrane. The potential of QSs for biological imaging is demonstrated by performing superresolution microscopy of the DiI-loaded vesicles in vitro and in cells. Therefore, fluorescent QSs constitute an appealing nanomaterial for bioimaging applications.

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“…The concentration of this surfactant is around the critical micelle concentration (CMC) 1.3 mM in water. 50 As shown in Fig. S2, † the morphology and structure of the Au NT@mSiO 2 particles changes as different amounts of additional CTAC are added to the growth solution.…”

Section: Resultsmentioning

confidence: 99%

Single-step coating of mesoporous SiO₂ onto nanoparticles: growth of yolk–shell structures from core–shell structures

2021

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The effect of anionic, cationic and neutral surfactants on the photophysics and isomerization of 3,3′-diethylthiacarbocyanine

Cited by 23 publications

References 44 publications

Isomerization and Properties of Isomers of Carbocyanine Dyes

Isomerization and Properties of Isomers of Carbocyanine Dyes

Nanostructuring Lipophilic Dyes in Water Using Stable Vesicles, Quatsomes, as Scaffolds and Their Use as Probes for Bioimaging

Single-step coating of mesoporous SiO₂ onto nanoparticles: growth of yolk–shell structures from core–shell structures

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The effect of anionic, cationic and neutral surfactants on the photophysics and isomerization of 3,3′-diethylthiacarbocyanine

Cited by 23 publications

References 44 publications

Isomerization and Properties of Isomers of Carbocyanine Dyes

Isomerization and Properties of Isomers of Carbocyanine Dyes

Nanostructuring Lipophilic Dyes in Water Using Stable Vesicles, Quatsomes, as Scaffolds and Their Use as Probes for Bioimaging

Single-step coating of mesoporous SiO2 onto nanoparticles: growth of yolk–shell structures from core–shell structures

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Single-step coating of mesoporous SiO₂ onto nanoparticles: growth of yolk–shell structures from core–shell structures