Syntheses and Properties of Cyanine and Related Dyes

Sturmer, David M.

doi:10.1002/9780470187005.ch8

Cited by 46 publications

(13 citation statements)

References 438 publications

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“…Cyanines have received in the class of polymethines big attention within the last hundred years [1][2][3][4]. Their substitution pattern easily facilitates shift of the absorption from the ultra violet part into the near infrared region while they exhibit huge extinction coefficients [3].…”

Section: Introductionmentioning

confidence: 99%

“…Nevertheless, cyanines have held a long history regarding their practical use, which started to use such materials as sensitizers in silver halide photography [32][33][34] until the point when electronic media took their place in imaging sciences to save pictures. Many fundamental knowledge was grown up in this period as shown for example by several reviews [35][36][37][38][39][40]. Particularly, the use of model systems and the knowledge obtained by exploration systems in silver halide photography [32][33][34][41][42][43][44][45] also helped to understand the function and formation H and J-aggregates [46][47][48][49] being aligned parallel or in series, respectively.…”

Section: Introductionmentioning

confidence: 99%

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Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

Strehmel¹,

Schmitz²,

Kütahya³

et al. 2020

Beilstein J. Org. Chem.

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Cyanines derived from heptamethines were mainly discussed regarding their functionalization to broaden the solubility in different surroundings exhibiting either hydrophilic or hydrophobic properties and to tailor made the ΔG et photopysical properties with respect to absorption and fluorescence. Electrochemical properties were additionally considered for some selected examples. The cyanines chosen comprised as end groups either indolenine, benzo[e]- or benzo[cd]indolium pattern, which facilitated to shift the absorption between 750–1000 nm. This enabled their use in applications with light sources emitting in the near-infrared (NIR) region selected from high power LEDs or lasers with line-shaped focus. The absorbers considered were discussed regarding their function as sensitizer for applications related to Chemistry 4.0 standards. These were mainly photopolymer coatings, which can be found for applications in the graphic industry or to protect selected substrates. The huge release of heat on demand upon turning ON or OFF the NIR light source enables them for photothermal treatment in processes requesting heat to initiate either chemical (activated reactions) or physical (melting, evaporation) events.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

Strehmel¹,

Schmitz²,

Kütahya³

et al. 2020

Beilstein J. Org. Chem.

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“…1 Since its discovery by Jelly 2 and Scheibe, 3 much attention has been paid to the J-aggregate from their structural features, 4-7 photographic process 8,9 nonlinear optical properties, 10,11 and multiple wavelength optical recording materials. 12 J-aggregates of cyanine dyes have been assembled in aqueous solutions, 2,3 in silver halide emulsions, 13,14 in solutions containing polyelectrolyte or salt, 15,16 and in films.…”

Section: Introductionmentioning

confidence: 99%

Spacer-Controlled Aggregation and Surface Morphology of a Selenacarbocyanine Dye on Gemini Monolayers

2006

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The adsorption and aggregation of a selenacarbocyanine dye (3,3-disulfopropyl-9-methyl-selenacarbocyanine, SeCy) onto Langmuir monolayers of a series of gemini amphiphiles with different methylene spacers were investigated. When the monolayers of the gemini amphiphiles were spread on the dye-containing subphase, the dye could be easily adsorbed and aggregated onto the monolayers through the electrostatic and pi-pi interaction. The dye formed complexes with gemini amphiphiles and stacked as J-aggregates in all the transferred multilayers, regardless of the structure of gemini amphiphiles. However, the surface morphologies of the complex monolayers showed a significant dependence on the spacer length of the gemini amphiphiles and the temperature of the subphase. Nanorods were observed for the complex films with spacer lengths ranged from 4 to 10 methylenes. With the temperature of the subphases increased from 20 degrees C to 30 degrees C, aligned longer nanofibers were formed instead. Although both the gemini amphiphiles and the dye were achiral, strong circular dichroism (CD) signals were observed for the transferred complex films. However, the CD signals could be just opposite in different places of the transferred films, suggesting that a resolved enantiomeric micro/nanostructure coexisted in the films. On the other hand, for the complex film of the dye with the gemini amphiphile of two methylenes spacer, neither CD signal nor ordered surface morphologies were detected in any place of the film although the dye itself stilled formed J-aggregate in the film. It was suggested that regular nanoarchitectures and resolved chiral domains could be observed only when the spacer of gemini amphiphiles is comparative to the distance between the two SO3- groups in the dye.

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“…In comparison, polymethine dyes are charged molecules, and their spectral properties are not significantly influenced by the solvent polarity [78]. In fact, cyanine and merocyanine dyes have been extensively used for fluorescence-labeling of protein, nucleic acid, and many other-of-interests in various biological applications because of their excellent photophysical properties, including superb fluorescence brightness (high quantum yields and molar absorbances), photostability, and long emission wavelengths without overlapping the cellular autofluorescence [79]. …”

Section: Cyanine (Polymethine) Dyesmentioning

confidence: 99%

Discovery of New Fluorescent Dyes: Targeted Synthesis or Combinatorial Approach?

Kim

Park

2010

Springer Series on Fluorescence

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Because of their advantageous properties, fluorescent organic molecules have been used extensively in various applications. Despite the high demand for fluorophores, there are only a limited number of fluorescent organic core skeletons with sufficient flexibility in their synthetic strategies. The rational design of fluorescent probes having desirable photophysical properties is still far from being achieved because of the complexity of underlying photophysical phenomena of fluorescent small molecules. To study and improve the photophysical properties of fluorescent core skeletons, many efforts have been pursued. Traditionally, targeted approach had been used to rationally study the photophysical properties of known fluorescent core skeleton. On the other hand, recent studies showed that combinatorial approach can act as a powerful tool to discover or develop novel fluorescent probes. Through a comparison between targeted synthesis and combinatorial approach in the study of fluorescent organic compounds, we can conclude that the targeted synthesis with rational design and systematic modification using combinatorial approach are complementary to each other for the discovery of novel, small molecules with desired photophysical properties.

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Syntheses and Properties of Cyanine and Related Dyes

Cited by 46 publications

References 438 publications

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

Spacer-Controlled Aggregation and Surface Morphology of a Selenacarbocyanine Dye on Gemini Monolayers

Discovery of New Fluorescent Dyes: Targeted Synthesis or Combinatorial Approach?

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