Styryl dye

A mesophenyl-substituted trimethine cyanine has been identified as a by-product in syntheses leading to styryl dyes it is also obtained when the anhydrobase reacts with the styryl dye (26). 

A rigidized molecule obtained when the two a-carbons of the trimethine chain are linked by a dimethylene bridge cannot be planar. According to the resonance concept, its stability increases as a bathochromic effect of 41 nm is observed (122). The of the bistyryl dye obtained by the substitution of the -proton in the chain of a styryl dye by a dialkylamino group is nearly the same as for the parent styryl dye (123). 

VII. Classification and List of Thiazolocyanine Dyes TABLE 1121 A, STYRYL DYES... 

Supramolecular organic photochemistry of crown-containing styryl dyes 97IZV641. 

Structural hybrid, in resonance theory. 69 Structures, of dyes, in relation with elecuo-chemical potential. 75 extreme of cyanine dyes, 69 Styryl compounds, nomenclature of, 29 Styryl dyes, in basicity scale, 71 with dialkylamino group, 77 as models in relation with pKa, 50 and role of anhvdrobases. 50 as sensitizers, in photography. 79 stereo aspect of condensation. 50 synthesis of, 49... 

Wang M, Gao M, Miller KD et al (2009) Simple synthesis of carbon-11 labeled styryl dyes as new potential PET RNA-specific, living cell imaging probes. Eur J Med Chem 44 2300-2306... 

R CHO aldehydes 1 pyridinium salts DMSO-EtOH 1V styryl dyes... 

Fig. 22 Synthetic schemes styryl scaffold-based DOFLA approach and building blocks and table for photophysical properties of synthesized styryl dye derivatives. Reproduced with permission from [90]...

Fig. 17 Chemical structure of the styryl dye (dibutylamino) stilbazolium butylsulfonate...

Wuskell JP, Boudreau D, Wei MD, Jin L, Engl R, Chebolu R, Bullen A, Hoffacker KD, Kerimo J, Cohen LB, Zochowski MR, Loew LM (2006) Synthesis, spectra, delivery and potentiometric responses of new styryl dyes with extended spectral ranges. J Neurosci Meth 151(2) 200-215... 

Hemicyanine (styryl) dyes are readily obtained by heating Fischer s base with an appropriate aldehyde. Typical products include Cl Basic Red 14 (6.224) and Cl Basic Violet 16 (6.225). The latter dye has been classified by ETAD as toxic [73]. 

This chapter describes the synthesis, properties, and biomedical applications of cyanine and squaraine dyes encapsulated in CDs, CBs, Leigh-type tetralactam macrocycles, aptamers, and micro- or nano-particles. The optical and photochemical properties of supramolecular guest-host nanostructures that are based on intra-and intermolecular complexes of crown-containing styryl dyes with metal cations, and aggregates of carbocyanine dyes are discussed in a separate review [18]. 

Reaction of 3-(9-julolidinyl)prop-2-en-l-al with N-( -adamantyl)-4-methyl-pyr-idinium chloride and a-CD in aqueous sodium hydroxide yielded styryl dye rotaxanes 6a and 7a as well as the free dye 8a (Fig. 5) [4, 27]. Analogously, the two rotaxane isomers 6b and 7b, and the free dye 8b were obtained from julolidine aldehyde and 4-methyl-2,6-diphenylpyridinium chloride. As compared to the hydrophobic dyes 8a, 8b, the rotaxanes 6a, 6b and 7a, 7b are highly soluble in water. The absorption/emission maxima of the rotaxanes 6a (525/710 nm) and 7a (535/718 nm) in DMSO are red-shifted compared to free styryl dye 8a... 

Analysis of the available literature data on host-guest complexes based on cyanine and styryl dyes with CDs shows that rotaxane formation in general... 

The squaraine rotaxane tetracarboxylic acid 15a is soluble in aqueous solution at physiological pH and acts as an excellent fluorescent marker with extremely high photostability, which allows trafficking processes in cells to be monitored in realtime, with constant sample illumination, over many minutes. This type of real-time monitoring cannot be done with other available NIR fluorescent probes, such as the amphiphilic styryl dye KM4-64 and water-soluble dextran-Alexa 647 conjugate, because they are rapidly photobleached. 

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