Studies on the Chemistry of Heterocyclics. Xx. The Absorption Spectra of Some Triarylmethane Dyes Containing a Thiophene Ring

Mason, C. D.; Nord, F. F.

doi:10.1021/jo01139a018

Cited by 13 publications

(6 citation statements)

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“…For those dyes which are the same as those made previously (11,12), the spectra and wavelength shifts obtained in this study in aqueous solution exhibit the same tendencies but are not identical in magnitude to those obtained by RiIason and Nord in acetic acid solutions (12 For personal use only.…”

Section: Eject Of Substitutionsupporting

confidence: 67%

“…As the success of the method depended greatly on the color of the dye produced it was of interest to ascertain the effect of various substituents attached to the thiophene ring on the spectra of the dyes. The effect of the replacement of the benzene nucleus by thiophene and a number of 5-substituted thiophene nuclei on triarylmethane dyes has been reported by Ailason and Nord (11,12). However, the present investig a t' ion enlarges on the previous studies by including a number of new mono-and di-substituted thienyl derivatives.…”

mentioning

confidence: 62%

“…Masoil and Nord (12) reported that the hypsochromic influence exerted on the x band increased with the size of the alkyl group. The total shift was 3 mp when the group size was increased from methyl to propyl.…”

Section: Eject Of Substitutionmentioning

confidence: 99%

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Triarylmethane Compounds as Redox Indicators in the Schoenemann Reaction: Iii. The Dyes and Their Spectra

Grant¹,

Blanchfield²,

Smith³

1958

Can. J. Chem.

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A series of triaryl~nethane dyes were made by varying the substituents in the thiophene ring of the dye [4-(p-dimethylamino-a-2-thienylbenzylidene)-2,5-cyclohexadiene-l-ylide~~e]-dimethylamlnonium chloride. The spectra of the zinc salts of these dyes were shown to be similar t o that of the dye formed in the Schoenemann reaction when the parent triarylmethane compound was used as a n indicator. Neither of the absorption bands occurring in the 475 mp or 625 mp regions is affected by pH or buffer salts in the pH range 2.4 to 6.4 but both bands are hypsochro~nically shifted when the pH is-lowered to 0.5. The substitution of 5-nitro and 5-acetamido groups in the thiophcne ring results in the largest bathochromic and hypsochromic shifts respectively. Interpretation of the effect of substitution and pH was attempted employing existing theories on the relation between color and constitution. INTRODUCTIOXThe preceding papers in this series (4, 14) described the preparation and use of some triarylmethane compounds as indicators in the Schoenemann reaction with a view to improving the method for detecting the phosphonofluoridate type of anticholinesterase compounds. As the success of the method depended greatly on the color of the dye produced it was of interest to ascertain the effect of various substituents attached to the thiophene ring on the spectra of the dyes. The effect of the replacement of the benzene nucleus by thiophene and a number of 5-substituted thiophene nuclei on triarylmethane dyes has been reported by Ailason and Nord (11,12). However, the present investig a t' ion enlarges on the previous studies by including a number of new mono-and di-substituted thienyl derivatives. The effect of pH on the spectra is also reported.I t was of interest to checlc the assumption that the oxidized compound produced in the Schoenernann reaction was the same as that of an authentic dye cation. Therefore spectral conlparisons have been made of a number of zinc chloride salts of prepared dyes with the dyes formed in the Schoenemann reaction. E X P E R I M E N T A L Preparation of DyesThe preparation and p~lrification of the triarylmethane compouilds from which the dyes were made have been described previously (4).The zinc chloride salts of the dyes were prepared from the correspoilding triarylmethane compounds according to the procedure of Mason and Nord (11) except that identical molar concentratioils of the solutions were always used in an attempt to produce salts of the same composition. The method of Davies and Hodgsoil (2) was investigated but was not found t o be superior to the method outlined by Ailason and Nord (11) or Levi (7).Briefly, the leuco compouilds (0.04 mole) were dissolved in 2 N HC1 (80 ml.) and the solutions were diluted with 800 ml. of water. Freshly prepared lead dioxide (0.04 mole) was added with stirring and cooling. After 2 hours sodium sulphate (0.05 mole) was 1Manz~script received J u l y 24, 1957.

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confidence: 67%

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confidence: 62%

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Triarylmethane Compounds as Redox Indicators in the Schoenemann Reaction: Iii. The Dyes and Their Spectra

Grant¹,

Blanchfield²,

Smith³

1958

Can. J. Chem.

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“…Observations consonant with this were made previously with MG derivatives bearing ortho and para methoxy substituents on the phenyl appendage, each revealing considerable y‐band redshifts relative to MG . Additional reports by Nord and Bengtsson illustrated y‐band redshifts for two thiophene TAMs ( 1 and 2 ).…”

Section: Introductionmentioning

confidence: 88%

“…Herein, we report the synthesis, optical properties and fluorogenic behaviors of seven highly colored, thiophene‐derived MGs, collectively termed MGTs, including a terthiophene, 3 , that exhibits radiative emission deep in the NIR region. Synthesis of compounds 1 and 2 was previously reported .…”

Section: Introductionmentioning

confidence: 99%

Spectral Properties of Fluorogenic Thiophene‐derived Triarylmethane Dyes

Stensrud

Zanotti

Waggoner

et al. 2018

Photochem & Photobiology

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Spectral properties and fluorogenic behaviors of five novel thiophene variants of Malachite Green (MG), termed MGTs, were determined. Appreciable changes as a function of homologation and substitution pattern, including absorption band positions and intensities and fluorescence quantum yields were observed. In particular, the shorter wavelength y-band absorption was found to shift over a nearly 200 nm range based on aryl group variation, allowing fine-tuning of the excitation wavelength for these dyes. In addition, the fluorescence intensity of some MGTs increased significantly (up to 4,600-fold) when the dye was bound to a cognate protein partner, which is potentially useful for cell imaging studies.

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Sulfamic Acid: A Recyclable Catalyst for the Synthesis of Triaryl‐ and Triheteroarylmethanes from Aldehydes and Activated Arenes

Liu

Yin

et al. 2018

ChemistrySelect

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A practical route to triarylmethanes: Sulfamic acid was found to efficiently catalyze Friedel–Crafts alkylations of 2‐methyl furan or 1, 2, 4‐trimethoxybenzene with a variety of simple or functionalized aldehydes to provide di‐ or triarylmethanes in high yields. The reaction tolerated variety of substitutions and functional groups under “open‐flask”, mild and solvent‐free conditions. Moreover, the Sulfamic acid can be conveniently recycled is especially noteworthy.

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Studies on the Chemistry of Heterocyclics. Xx. The Absorption Spectra of Some Triarylmethane Dyes Containing a Thiophene Ring

Cited by 13 publications

References 10 publications

Triarylmethane Compounds as Redox Indicators in the Schoenemann Reaction: Iii. The Dyes and Their Spectra

Triarylmethane Compounds as Redox Indicators in the Schoenemann Reaction: Iii. The Dyes and Their Spectra

Spectral Properties of Fluorogenic Thiophene‐derived Triarylmethane Dyes

Sulfamic Acid: A Recyclable Catalyst for the Synthesis of Triaryl‐ and Triheteroarylmethanes from Aldehydes and Activated Arenes

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