Abstract
Although the first hydroxy substituted triphenlymethane dyes were prepared at the beginning of the 19th century, they found, other than their amino-substituted derivatives, surprisingly less scientific and practical interest hitherto. Only triphenylmehane dyes derived from salicylic acid and some of its derivatives received practical importance as Mordant Dyes. To close this gap, we have prepared and characterized few hydroxy-substituted triphenlymethane dyes by starting from appropriate phenols and using different synthetic routes. The structure of the hydroxy-substituted triphenlymethane dyes prepared are confirmed by means of mass spectra and 1H NMR spectra. Their colors vary with the acidity of the solutions and is originated by a stepwise protonation of the oxygen moieties at their triphenylmethane cores.
Funding source: There is no funding
Acknowledgments
The author thanks Dr. S. Machill for measuring the absorption spectra, Mrs. A. Rudolph for measuring the 1H HMR spectra and Dr. I. Bauer for measuring the mass spectra.
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Research ethics: Not applicable.
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Informed consent: Not applicable.
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Author contributions: The author has accepted responsibility for the entire content of this manuscript and approved its submission.
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Use of Large Language Models, AI and Machine Learning Tools: None declared.
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Conflict of interest: The author states no conflict of interest.
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Research funding: None declared.
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Data availability: Not applicable.
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Honorarium: Dedicated to Dr. Alfred Keil on the occasion of his 100th birthday.
References
1. Runge, F. F. Ueber einige Produkte der Steinkohlendestillation. Ann. Phys. Chem. 1934, 31, 65–80; https://doi.org/10.1002/andp.18341070502.Search in Google Scholar
2. Runge, F. F. Ueber einige Producte der Steinkohlendestillation. Ann. Phys. Chem. 1934, 31, 513–524; https://doi.org/10.1002/andp.18341073302.Search in Google Scholar
3. Kolbe, H.; Schmitt, R. Roter Farbstoff aus Kreosot. Liebigs Ann. Chem. 1861, 119, 169–176.10.1002/jlac.18611190207Search in Google Scholar
4. Color Index British Society of Dyers and Colourist; Pickersgill, Ltd.: Chorley, 1957.Search in Google Scholar
5. Dale, R. S.; Schorlemmer, C. Ueber das Aurin. Ber. Dtsch. Chem. Ges. 1871, 4, 574–576; https://doi.org/10.1002/cber.18710040218.Search in Google Scholar
6. Hofmann, A. W. Ueber Farbabkömmlinge der Pyrogallussäure-Äther. Ber. Dtsch. Chem. Ges. 1878, 11, 1455–1461; https://doi.org/10.1002/cber.18780110252.Search in Google Scholar
7. Reichenbach, K. Ueber das Kreosot, ein neues Product der trockenen Destillation organsicher Körper. Journal für Chemie und Physik 1832, 65, 461–462.Search in Google Scholar
8. Reichenbach, K. Beiträge zur näheren Kenntnis der trockenen Destillation organischer Körper, das Kreosot. Journal für Chemie und Physik 1832, 66, 301–322.Search in Google Scholar
9. Reichenbach, K. Beiträge zur näheren Kenntnis der trockenen Destillation organischer Körper. Journal für Chemie und Physik 1832, 66, 345–362.Search in Google Scholar
10. Reichenbach, K. Beiträge zur näheren Kenntnis der trockenen Destillation organischer Körper. Journal für Chemie und Physik 1833, 67, 1–25.10.1002/prac.18340010171Search in Google Scholar
11. Reichenbach, K. Beiträge zur näheren Kenntnis der trockenen Destillation organischer Körper, einige Beispiele schätzbarer Heilwirkungen des Kreosots. Journal für Chemie und Physik 1833, 67, 57–72.Search in Google Scholar
12. Reichenbach, K. Beiträge zur näheren Kenntnis der trockenen Destillation organischer Körper, über die Heilwirkung und Bereitung des Kreosots. Journal für Chemie und Physik 1833, 68, 399–419.Search in Google Scholar
13. Liebermann, C. Über Eupitton und Pittakal. Ber. Dtsch. Chem. Ges. 1901, 34, 1026–1030; https://doi.org/10.1002/cber.190103401168.Search in Google Scholar
14. Liebermann, C.; Wiedermann, F. Ueber Eupittonderivate. Ber. Dtsch. Chem. Ges. 1901, 34, 1031–1040; https://doi.org/10.1002/cber.190103401169.Search in Google Scholar
15. Elbs, K. Einige Synthesen mit Chlorpikrin Mittels Chloraluminium. Ber. Dtsch. Chem. Ges. 1883, 16, 1274–1277; https://doi.org/10.1002/cber.188301601284.Search in Google Scholar
16. Hartmann, H. The Historical Dyestuff Collection at the Technical University Dresden: A Cultural-Historical Treasure and a Rich Source of Light-Absorbing Materials with Great Prospects for Current and Future Research. ChemPhotoChem 2021, 5, 619–625; https://doi.org/10.1002/cptc.202100017.Search in Google Scholar
17. Hartmann, H. On the Discovery of the First Synthetic Dyes Prepared from Phenolic Tar Ingredients. J. Chem. Res. 2024, 8, 1–10; https://doi.org/10.1177/17475198241262008.Search in Google Scholar
18. Shokrollahi, A.; Gohari, M.; Ebrahimi, F. Determination of Acidity Constants of P-Rosolic Acid and Bromxylenol Blue by Solution Scanometric Method. Anal. Bioanal. Chem. Res. 2018, 5, 67–79.Search in Google Scholar
Supplementary Material
This article contains supplementary material (https://doi.org/10.1515/znb-2024-0112).
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Articles in the same Issue
- Frontmatter
- In this issue
- Research Articles
- Chemical aspects of the preparation of Vulcanised Fibre using zinc chloride hydrates: from a brief history to a new consideration of the key reactions in ionic liquids
- On the preparation and spectral properties of some hydroxy-substituted triphenylmethane dyes
- High-pressure synthesis and crystal structure of Ga5Na1–x B12O26–x (OH) x (x = 0.12)
- Intermetallic phases with Ho4Ir13Ge9-type structure
- Interplay between oxidative addition and reductive elimination at a diruthenium complex bearing the bis(diphenylphosphanyl)amine ligand
- Anthracene-d- and l-phenylalanine derivatives: synthesis, dual-state emission, mechanochromic luminescence, chiroptical property and enantioselective recognition of free amino acids
- Synthesis, structures and optical properties of 3,3′-disubstituted biphenyl compounds