Styryl bases

Rettig W, Rurack K, Sczepan M (2001) From cyanines to styryl bases - photophysical properties, photochemical mechanisms, and cation sensing abilities of charged and neutral polymethinic dyes. In Valeur B, Brochon JC (eds) New trends in fluorescence spectroscopy applications to chemical and life sciences. Springer, Berlin, pp 125-155... 

From Cyanines to Styryl Bases -Photophysical Properties, Photochemical Mechanisms, and Cation Sensing Abilities of Charged and Neutral Polymethinic Dyes, in Valeur B. and Brochon J. C. (Eds),... 

E. U. Akkaya and J. R. Lakowicz, Styryl-based wavelength ratiometric probes A new class of fluorescent calcium probes with long wavelength emission and a large stokes shift, Anal. Biochem. 213, 285-289 (1993). 

Table 4. Summary of block copolymers prepared using nitroxide-mediated polymerizations that contain one non-styryl-based block...

Styryl bases such as -diethylaminostyrylquinoline can be activated by carbon tetrabromlde (145). The image dye has been shown to consist of about 75% hydrobromide of the styryl base and of 25% of the quaternary dimer. 

Several series of styryl-based dyes incorporating thia-crown ether moieties (e.g., II) have been prepared and smdied as selective optical sensors for heavy metal ions in aqueous solutions. 

Haddad TS, Lichtenhan JD (1996) Hybrid organic-inorganic thermoplastics Styryl-based polyhedral oligomeric silsesquioxane polymers. Macromolecules 29(22) 7302-7304. doi 10.1021/Ma960609d... 

In styryl compounds, a part of the methine chain is replaced by a phenyl group. Their name is based on the nuclei from which they are issued 3-ethyl-5-methyl-2-(p-dimethylaminostyryl)thiazolium iodide (Scheme 7). 

Styryl Derivatives of Benzene and Biphenyl. Othei compounds based on the styryl gioup weie piepaied to lengthen the conjugated system of stilbene. 

Dyes, polymethine used for dyes having at least one electron donor and one electron acceptor group linked by methine groups or aza analogues aUopolar cyanine, dye bases, complex cyanine, hemicyanine, merocyanine, oxonol, streptocyanine, and styryl. Supersensitization has been reported for these types—18 cites for cyanines, 3 for merocyanine, and 6 for all other polymethine types. 

With l,3-dimethyl-2,l-benzisoxazolium salts, however, considerable reactivity has been reported. Condensation occurs readily with aldehydes, ketones, orthoesters and diazonium salts to yield styryl, cyanine and azo compounds, respectively (78JOC1233). In the presence of triethylamine, dimerization was observed, and the reactions of the cation were considered to involve the intermediacy of the anhydro base (77JOC3929). 

Aliphatic and aromatic aldehydes condensed with 2-amino-(62BRP898414), 5-amino- (80AJC1147), or 8-amino-l,2,4-triazolo[l,5-cjpyrimidines (68JOC530) to give the related Schiff bases. Treatment of the 2-amino-5-methyl-l,2,4-triazolo[l,5-c]quinazoline 11 with formaldehyde and piperidine in the presence of acetic acid gave the 2-hydroxymethyl-amino-5-(2-piperidinoethyl) derivative 172. Utilization of aromatic aldehydes and piperidine in this reaction gave the 2-arylideneamino-5-styryl derivatives 173 (68CB2106) (Scheme 67). 

The 2-methyl group of 2-methyl-3T/-azepines, e.g. 11, is surprisingly reactive and undergoes rapid deuterium exchange and, in the presence of base, aldol condensation with areneal-dehydes to yield styryl derivatives, e.g. 12.76108... 

As well as phenyl derivatives, other products have been prepared by hydrolysis of alkoxysilanes such as cyclohexenyl or naphthyl derivatives as well as heterocyclic compounds based on thienyl rings (Table 31, entries 28-33). Few practical applications have been reported for this type of compound, except for the styryl compound T81C6H4-A-CFI = CH2]s, and the fluorinated TslCeFsJs which have been used in polymer blending (Table 31, entries 13 and 28). ... 

This next example involves the well-known plant kawa. A psychoactive beverage made from the roots of this plant is used widely in the islands of the southwestern Pacific Ocean either for ritualistic or routine consumption. Kava is the common name for Piper methysticum Forst. f. from which several compounds responsible for the pharmacological activity have been isolated and identified. Representative structures of the family of styrylpyrones, commonly called kavalactones, are given in Fig. 6.6. The compounds are based upon a carbon skeleton consisting of a styryl function (C C ) attached to a six-membered lactone ring. The fundamental compound, kawain, is shown as structure [547]. Structural variants include... 

Quinone methides formed during, for example, alkaline pulping reactions may have other mechanisms for rearomatization. Most commonly, in 8-0-4-, 8-5-, and 8-8-quinone methides QM1-QM3 (Fig. 12.2), retro-aldol elimination of formaldehyde to give styryl aryl ethers or stilbenes is common.40 Retro-aldol reactions using a strong base, for example, diazabicycloundecene (DBU) in CH2CI2 can also provide these compounds conveniently at room temperatures.41 3... 

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]...

Rosania GR, Lee JW, Ding L, Yoon HS, Chang YT (2003) Combinatorial approach to organelle-targeted fluorescent library based on the styryl scaffold. J Am Chem Soc 125 1130-1131... 

Photocrosslinking. The second class of photopolymer chemistry that is used in some commercial products is based on the reaction of unsaturated moieties attached to an organic polymer. These photopolymer materials include the [2+2] cycloaddition of the ethylenic groups in poly(vinyl cinnamate) polymers and in the newer styryl pyridinium (10) and thiazolium (77) derivatives of poly(vinyl alcohol). The main advantage of this chemistry is that, unlike free-radical photopolymerization, they are insensitive to the presence of oxygen. This photopolymer mechanism is principally used in applications employing a washout development process (e.g. resists). 

The biomimetic protocol was invented by Julia and Colonna, and involves the use of polyamino acids (such as poly-(L)-leucine) as the catalysts for peroxide oxidation of chalcones, styryl alkyl ketones and conjugated alkenones. The substrate range is broad, especially when using immobilized catalysts and an organic solvent containing the substrate, urea-hydrogen peroxide and an organic base (Scheme 22)[101]. 

TPAs bearing cross-linkable oxetane functionalities (52) (Scheme 3.20) has been developed [95,96], This material can be easily photo-patterned by exposure to a very short wavelength UV light source to form a patterned and insoluble HTL. Similar photo-cross-linkable HTMs based on side-chain acrylate or styryl functional groups have been synthesized (53,54) [97]. A series of spiro-linked and photo-cross-linkable HTMs have been patented by the Canon group [98]. 

Recently, Chen s group reported a deep blue OLED based on an asymmetric mono(styryl) amine derivative DB1 (192) as shown in Scheme 3.59. PL spectra of this deep blue dopant in toluene solution showed a peak emission of 438 nm, which is about 20 nm hypsochromic shift compared with DSA-amine symmetric dopant, due to the shorter chromophoric conjugated length of the mono(styryl) amine. OLED device based on this blue dopant achieved a very high efficiency of 5.4 cd/A, with CIE coordinates of (0.14, 0.13) [234]. 

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