Synthesis of thiapenta- and thiahexacarbocyanine dyes from alkoxy-substituted polymethine salts with dimethylamine residues

Monich, N. V.; Krasnaya, Zh. A.; Levkoev, I. I.; Kucherov, V. F.

doi:10.1007/bf00506991

Cited by 3 publications

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References 2 publications

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“…However, the low fluorescence quantum yield, short fluorescence lifetime, propensity to photobleach, and poor chemical stability of these dyes have limited their use in chemical and life sciences. To overcome these limitations, numerous studies have shown that incorporating a rigid cyclohexenyl ring in the polymethine chain increases photostability and enhances the quantum yield in comparison to cyanine dyes with an open polymethine chain. − The central cyclohexenyl group offers an additional reactive site for labeling bioactive molecules via functionalization of the meso -chloro cyclohexenyl group. Furthermore, incorporating the alkylsulfonato functionality on the nitrogen atom of the heterocyclic moiety improves photostability and water solubility.…”

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confidence: 99%

Heptamethine Cyanine Dyes with a Robust C−C Bond at the Central Position of the Chromophore

2006

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Novel, highly fluorescent, monofunctional, water-soluble heptamethine cyanine dyes containing a robust C−C bond at the central position of the near-infrared fluorophore system were prepared by the Suzuki−Miyaura method. The reaction proceeded efficiently to replace the meso-chlorine atom with a carboxy-functionalized aryl moiety and afforded the desired compounds in high yields. This methodology is particularly attractive due to its versatility and the utilization of environmentally friendly water as solvent. The new compounds possess excellent spectral properties and readily label bioactive molecules on solid support. The results demonstrate the potential of using the new compounds as fluorescent antennae for molecular imaging, spectroscopy, microscopy, and chemical or biological molecular recognition studies.

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confidence: 99%

Heptamethine Cyanine Dyes with a Robust C−C Bond at the Central Position of the Chromophore

2006

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“…An important class of the bioanalytical markers are cyanines containing a ring structure at the center of the chromophore (Chart). The partial rigidization of the molecule increases not only stability but also fluorescence efficiency [11,15,16]. The chloro-substituted dyes, such as 1 -4, are easily synthesized and purified by crystallization (no chromatography), and they serve as precursors to other meso-substituted dyes [17][18][19].…”

Section: Remarkable Stabilities In Solutionmentioning

confidence: 99%

Stability in solution of indolium heptamethine cyanines and related pH‐sensitive systems

Strękowski

Mason

Say

et al. 2007

Journal of Heterocyclic Chem

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Theoretical Models, Preparation, Characterization and Applications of Cyanine J‐Aggregates: A Minireview

Dar

Ankari

2022

ChemistryOpen

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Cyanines are one of the few kinds of molecules whose absorbance and emission can be shifted in a broad spectral range from the ultraviolet to the near infrared. They can easily transform into J‐aggregates with narrow absorption and emission peaks, along with a redshift in their spectra. This mini‐review presents cyanine dyes and their J‐aggregates and discusses their structure and spectral properties that illustrate their specificities. We summarize the theoretical and experimental state of the art on cyanine J‐aggregates and their applications, also laying the groundwork for cyanine J‐aggregates synthesis and characterization methods.

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Synthesis of thiapenta- and thiahexacarbocyanine dyes from alkoxy-substituted polymethine salts with dimethylamine residues

Cited by 3 publications

References 2 publications

Heptamethine Cyanine Dyes with a Robust C−C Bond at the Central Position of the Chromophore

Heptamethine Cyanine Dyes with a Robust C−C Bond at the Central Position of the Chromophore

Stability in solution of indolium heptamethine cyanines and related pH‐sensitive systems

Theoretical Models, Preparation, Characterization and Applications of Cyanine J‐Aggregates: A Minireview

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