Chemistry:Rhodamine B

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Rhodamine B
Rhodamine B.svg
Names
Preferred IUPAC name
9-(2-Carboxyphenyl)-6-(diethylamino)-N,N-diethyl-3H-xanthen-3-iminium chloride
Other names
Rhodamine 610, C.I. Pigment Violet 1, Basic Violet 10, C.I. 45170
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
Properties
C28H31ClN2O3
Molar mass 479.02
Appearance red to violet powder
Melting point 210 to 211 °C (410 to 412 °F; 483 to 484 K) (Decomposes)
8 to 15 g/L (20 °C)[1][nt 1]
Hazards
Safety data sheet MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Rhodamine B /ˈroʊdəmiːn/ is a chemical compound and a dye. It is often used as a tracer dye within water to determine the rate and direction of flow and transport. Rhodamine dyes fluoresce and can thus be detected easily and inexpensively with fluorometers.

Rhodamine B is used in biology as a staining fluorescent dye, sometimes in combination with auramine O, as the auramine-rhodamine stain to demonstrate acid-fast organisms, notably Mycobacterium. Rhodamine dyes are also used extensively in biotechnology applications such as fluorescence microscopy, flow cytometry, fluorescence correlation spectroscopy and ELISA.[citation needed]

Other uses

Rhodamine B solution in water

Rhodamine B is often mixed with herbicides to show where they have been used.[2]

It is also being tested for use as a biomarker in oral rabies vaccines for wildlife, such as raccoons, to identify animals that have eaten a vaccine bait. The rhodamine is incorporated into the animal's whiskers and teeth.[3] Rhodamine B is an important hydrophilic xanthene dye well known for its stability and is widely used in the textile industry, leather, paper printing, paint, coloured glass and plastic industries.[4]

Rhodamine B (BV10) is mixed with quinacridone magenta (PR122) to make the bright pink watercolor known as Opera Rose.[5]

Properties

A is the "open" form and B is the "closed" form
Rhodamine B closed form (A) and open form (B)

Rhodamine B can exist in equilibrium between two forms: an "open"/fluorescent form and a "closed"/nonfluorescent spirolactone form. The "open" form dominates in acidic condition while the "closed" form is colorless in basic condition.[6]

The fluorescence intensity of rhodamine B will decrease as temperature increases.[7]

The solubility of rhodamine B in water varies by manufacturer, and has been reported as 8 g/L and ~15 g/L,[1] while solubility in alcohol (presumably ethanol) has been reported as 15 g/L.[nt 1] Chlorinated tap water decomposes rhodamine B. Rhodamine B solutions adsorb to plastics and should be kept in glass.[8] Rhodamine B is tunable around 610 nm when used as a laser dye.[9] Its luminescence quantum yield is 0.65 in basic ethanol,[10] 0.49 in ethanol,[11] 1.0,[12] and 0.68 in 94% ethanol.[13] The fluorescence yield is temperature dependent;[14] the compound is fluxional in that its excitability is in thermal equilibrium at room temperature.[15]


Safety and health

In California, rhodamine B is suspected to be carcinogenic and thus products containing it must contain a warning on its label.[16] Cases of economically motivated adulteration, where it has been illegally used to impart a red color to chili powder, have come to the attention of food safety regulators.[17]

See also

References

  1. ↑ 1.0 1.1 "Safety data sheet". Roth. 2013. https://www.carlroth.com/medias/SDB-T130-AU-EN.pdf?context=bWFzdGVyfHNlY3VyaXR5RGF0YXNoZWV0c3wyMzk1MjZ8YXBwbGljYXRpb24vcGRmfHNlY3VyaXR5RGF0YXNoZWV0cy9oYjEvaDUxLzg5Njk3MDM2ODYxNzQucGRmfDg5ZTFiNGZmNDIzMzc3NDczZjhlYjA3ODBmY2JiOTBkODkyNDc3ZWI3NDU0ODJiNTBmMWM1ZjAzNDI4NDZhMjQ. 
  2. ↑ "Evaluation of five fluorescent dyes and triethyl phosphate as atmospheric tracers of agricultural sprays". Journal of Environmental Science and Health, Part B 32 (6): 969–83. November 1997. doi:10.1080/03601239709373123. Bibcode: 1997JESHB..32..969C. 
  3. ↑ "Oral rabies vaccination in north america: opportunities, complexities, and challenges". PLOS Neglected Tropical Diseases 3 (12): e549. December 2009. doi:10.1371/journal.pntd.0000549. PMID 20027214. 
  4. ↑ Sudarshan, Shanmugam; Bharti, Vidya Shree; Harikrishnan, Sekar; Shukla, Satya Prakash; RathiBhuvaneswari, Govindarajan (2 October 2022). "Eco-toxicological effect of a commercial dye Rhodamine B on freshwater microalgae Chlorella vulgaris". Archives of Microbiology 204 (10): 658. doi:10.1007/s00203-022-03254-5. PMID 36183287. Bibcode: 2022ArMic.204..658S. 
  5. ↑ MacEvoy, Bruce. "Handprint: color making attributes". www.handprint.com. http://www.handprint.com/HP/WCL/waterc.html. 
  6. ↑ "Investigating rhodamine B-labeled peptoids: scopes and limitations of its applications". Biopolymers 96 (5): 694–701. 2011. doi:10.1002/bip.21617. PMID 22180914. 
  7. ↑ "Thermo-optical characterization of fluorescent rhodamine B based temperature-sensitive nanosensors using a CMOS MEMS micro-hotplate". Sensors and Actuators. B, Chemical 192: 126–133. March 2014. doi:10.1016/j.snb.2013.10.042. PMID 25844025. 
  8. ↑ Bedmar, Antonio Plata; Araguás, Luís Araguás (2002). Detection and Prevention of Leaks from Dams. Taylor & Francis. ISBN 90-5809-355-7. 
  9. ↑ Prahl, Scott. "Rhodamine B". OMLC. http://omlc.ogi.edu/spectra/PhotochemCAD/html/rhodamineB.html. 
  10. ↑ "Fluorescence quantum yields of some rhodamine dyes". Journal of Luminescence 27 (4): 455–462. 1982. doi:10.1016/0022-2313(82)90045-X. Bibcode: 1982JLum...27..455K. http://habana.qfa.uam.es/~lmc/ref/old/kubin82.pdf. 
  11. ↑ Casey, Kelly G.; Quitevis, Edward L. (1988). "Effect of solvent polarity on nonradiative processes in xanthene dyes: Rhodamine B in normal alcohols". The Journal of Physical Chemistry 92 (23): 6590–6594. doi:10.1021/j100334a023. 
  12. ↑ "Radiationless Intermolecular Energy Transfer. III. Determination of Phosphorescence Efficiencies". The Journal of Chemical Physics 41 (10): 3042–3045. 1964. doi:10.1063/1.1725672. Bibcode: 1964JChPh..41.3042K. 
  13. ↑ "The photophysics of rhodamine B". Journal of Photochemistry 18 (4): 335–346. 1982. doi:10.1016/0047-2670(82)87023-8. 
  14. ↑ "Rhodamine B and rhodamine 101 as reference substances for fluorescence quantum yield measurements". The Journal of Physical Chemistry 84 (14): 1871–1872. 1980. doi:10.1021/j100451a030. 
  15. ↑ "Bypassing bleaching with fluxional fluorophores". Nature Methods 16 (5): 357. May 2019. doi:10.1038/s41592-019-0402-2. PMID 31040423. (Subscription content?)
  16. ↑ "Naval Jelly MSDS with Rhodamine B". Locite Corporation. 20 October 1998. http://www.brown.edu/Departments/Visual_Art/documents/NavalJelly.pdf. 
  17. ↑ Lin, Shuang (2015). "Rapid and sensitive SERS method for determination of Rhodamine B in chili powder with paper-based substrates". Analytical Methods 7 (12): 5289. doi:10.1039/c5ay00028a. https://www.researchgate.net/publication/278036259. Retrieved 1 February 2018. 

Notes

  1. ↑ 1.0 1.1 Ellis, Roy C. (November 16, 2015). "Reagent and Dye Solubility Chart". IHCWorld. http://www.ihcworld.com/_technical_tips/solubility_chart.htm. "This is to be used as a guide only as solubility data varies between manufacturers for the same product, especially for dyes."  Note that most sources simply indicate that the compound is water soluble without providing a g/L value.



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