The synthesis, structure and spectral properties of new long-wavelength benzodipyrroleninium-based bis-styryl dyes

Fedyunyayeva, Iryna A.; Klochko, Oleksii P.; Semenova, O.; Khabuseva, S.U.; Povrozin, Yevgen A.; Sokolyk, Oksana O.; Stepanenko, Olena Yu.; Terpetschnig, Ewald; Patsenker, L. D.

doi:10.1016/j.dyepig.2010.12.004

Cited by 7 publications

(8 citation statements)

References 29 publications

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“…e absorption maxima are mainly dominated by the nature of the excited state -electron system. As well known, a strong electron donor could help to stabilize the charge-separated excited state of the molecule; the red-shi could be explained by the electron-donating strength of donor group [35,46].…”

Section: Resultsmentioning

confidence: 95%

“…As a result, the dyes 6b-n were bathochromic shi of 11-76 nm. It can be seen from Table 3 that that should produce a bathochromic shi of max [46]. In general, with respect to the substituents R of dyes 6b, 6e, 6l, and 6n, the dyes were bathochromically shied in the following order: diethylaminophenyl (6e) (Δ max 76 nm)>diphenylaminophenyl (6n) (Δ max 58 nm)>dimethylaminophenyl (6b) (Δ max 43 nm)>4acetamidophenyl (6l) (Δ max 41 nm).…”

Section: Resultsmentioning

confidence: 97%

“…According to Richter [48] and McLaren et al [49] the position of the color is distributed in the red-green area with hue angle ℎ ∘ 33.07-116.83 ∘ and radial chroma * of length 8. [35][36][37][38][39][40][41][42][43][44][45][46][47][48].08. Figure 1 shows a graph of CIE coordinates * versus * for selected dyes 6b, 6e, 6l, and 6n (an increasing * value represents an increase in redness, while a decrease in * represents a green hue shi).…”

Section: Dyeing and Fastnessmentioning

confidence: 99%

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Thioxopyrimidine in Heterocyclic Synthesis III: Synthesis and Properties of Some Novel Heterocyclic Chalcone Derivatives Containing a Thieno[2,3‐d]pyrimidine‐Based Chromophore

Ho¹,

Yao

2013

Journal of Chemistry

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Cyclization of 4-methyl-2-phenyl-6-thioxo-1,6-dihydropyrimidine-5-carbonitrile1with chloroacetone in DMF in the presence of excess potassium carbonate anhydrous gave the 1-(5-amino-4-methyl-2-phenylthieno[2,3-d]pyrimidin-6-yl)ethanone3, which can react with 2,5-dimethoxytetrahydrofuran in glacial acetic acid producing the 1-[4-methyl-2-phenyl-5-(1H-pyrrol-1-yl)thieno[2,3-d]pyrimidin-6-yl]ethanone4. On the other hand, a series of novel 3-aryl-1-[4-methyl-2-phenyl-5-(1H-pyrrol-1-yl)-thieno[2,3-d]pyrimidin-6-yl]prop-2-en-1-one chalcone dyes6a—nwere obtained by the condensation reaction of 1-[4-methyl-2-phenyl-5(1H-pyrrol-1-yl)thieno[2,3-d]-pyrimidin-6-yl]ethanone4with appropriate aldehydes. The structures of chalcone dyes were characterized by IR,1H NMR, mass, elemental analysis, and UV-Vis spectroscopy. The dyes were applied to polyester fibers for creating hues ranging from greenish-yellow to orange; their spectral characteristics, substituent effect in DMF solution, fastness properties, and colorimetric assessment are also discussed.

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Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 97%

Section: Dyeing and Fastnessmentioning

confidence: 99%

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Thioxopyrimidine in Heterocyclic Synthesis III: Synthesis and Properties of Some Novel Heterocyclic Chalcone Derivatives Containing a Thieno[2,3‐d]pyrimidine‐Based Chromophore

Ho¹,

Yao

2013

Journal of Chemistry

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“…The presence of a julolidinium moiety (dyes 5 and 16 ) results in an increase of the conformational rigidity of dye structure. The molecules containing julolidinium, piperidinium, morpholinium and pyrrolidinium moieties (dyes 5 , 6 , 10 , 11 , 14 , 16 and 17 ) become less flexible and statistically more planar in comparison with dyes containing a dialkylamino moiety [52].…”

Section: Resultsmentioning

confidence: 99%

A novel general method for fast and easy preparation of cationic, neutral dimethinehemicyanine and dimethine dyes by uncatalysed Knoevenagel condensation

Deligeorgiev

Gadjev

Kaloyanova

et al. 2012

Coloration Technology

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Three novel general experimental procedures for preparation of cationic, neutral dimethinehemicyanine and dimethine dyes (eight of which are unpublished) by uncatalysed Knoevenagel condensation have been developed. The proposed methods are versatile as a variety of different starting materials can be used and they ensure good to very high yields, very short reaction times and high purity of the final dyes. Absorption and fluorescent properties of the novel dyes were investigated.

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“…[34,35] Since 3 and 4 bearing activated methyl group can act as nucleophile and be used for the syntheses of bis-styryle dyes and bis-cyanine dyes, they can react with squaric acid and its derivative. [36][37][38] The condensation of N,Ndibutylaniline and 1,2-dichlorocyclobuten-3,4-dion, obtained by the reaction of squaric acid with oxalyl chloride and subsequent hydrolysis reaction, yielded monosubstituted squaric acid (2). [2.39,40] Condensation reactions of benzodipyrrole derivatives 3 and 4 with 2 afforded BS1 and BS2 in yields of 41% and 37%, respectively.…”

Section: Synthesis and Structurementioning

confidence: 99%

Synthesis, Photophysical and Electrochemical Properties of Bis‐Squaraine Dyes Fused on Isomeric Benzodipyrrole Central Units

Sawada

Maeda

Oda

et al. 2022

Chemistry An Asian Journal

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Exciton interactions are not only observed in assembled molecules but also in compounds with multiple chromophores referred to as superchromophores. We have developed isomeric bis-squaraine dyes as superchromophores in which two squaraine chromophores are fused onto the isomeric benzodipyrrole skeleton so as to regulate conformations and to reduce distances between two chromophores. The dyes with benzo[1,2-b:3,4-b']dipyrrole and benzo[1,2-b:5,4-b']dipyrrole moieties exhibited split electronic absorption originated from the intramolecular exciton inter-action. The intensity of the split absorption bands varies in correlation with the orientation of chromophores. The isomeric dye with benzo[1,2-b:4,5-b']dipyrrole moiety exhibited a near-infrared absorption associated with the resonance throughout two chromophores. Their electrochemical and spectroelectrochemical properties are distinct from those of monomeric dyes owing to electronic interactions between the two chromophores. Thus, the structural isomerism of the central skeleton significantly affects their optical properties as well as their electrochemical properties.

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The synthesis, structure and spectral properties of new long-wavelength benzodipyrroleninium-based bis-styryl dyes

Cited by 7 publications

References 29 publications

Thioxopyrimidine in Heterocyclic Synthesis III: Synthesis and Properties of Some Novel Heterocyclic Chalcone Derivatives Containing a Thieno[2,3‐d]pyrimidine‐Based Chromophore

Thioxopyrimidine in Heterocyclic Synthesis III: Synthesis and Properties of Some Novel Heterocyclic Chalcone Derivatives Containing a Thieno[2,3‐d]pyrimidine‐Based Chromophore

A novel general method for fast and easy preparation of cationic, neutral dimethinehemicyanine and dimethine dyes by uncatalysed Knoevenagel condensation

Synthesis, Photophysical and Electrochemical Properties of Bis‐Squaraine Dyes Fused on Isomeric Benzodipyrrole Central Units

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