Rhodamine & Rhodanine explanation12.pptx

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1. Rhodamine & Rhodanine Presented by: Hadeel Fawzi Hammad

2. (1) Rhodamines

3. Occurance : Rhodamine is a family of related dyes. A subset of the  triarylmethane dyes . They are derivatives of   xanthene .  Important members of the rhodamine family are  Rhodamine 6G ,  Rhodamine 123 , and  Rhodamine B

4. Synthesis : The synthesis of pure rhodamine dyes from phthalaldehydic acids with 3-( dimethylamino )phenol .

5. Reactions: By the reaction of rhodamine 6G in MeOH , hydrazine hydrate and phenyl isothiocyanate then addition of acetonitrile and mercury II perchlorate hydrate , Rhodamine 6G hydrazide was prepared

6. Applications: They are often used as a  tracer dye to determine the rate and direction of flow and transport of water. Rhodamine dyes  fluoresce  and can be detected easily and inexpensively with instruments called  fluorometers . Rhodamine dyes are used extensively in biotechnology applications such as  fluorescence microscopy ,  flow cytometry ,  fluorescence correlation spectroscopy  and  ELISA . Rhodamines are used in  dye laser   as  gain media . They are mainly used to dye paper and inks, but they lack the  light fastness  for fabric dying .

7. (2) Rhodanines

8. Occurance : Rhodanine  is a 5-membered  heterocyclic   organic compound  possessing a  thiazolidine  core.

9. Synthesis : Rhodanine and its derivatives can be directly prepared via the reaction of thiourea and thioglycolic acid in one step catalyzed by protic acid.

10. Synthesis: And also can be directly prepared via the three-component coupling of carbon disulfide , primary amines , and acetylenic esters under neutral conditions in water.

11. Reactions: Knoevenagel condensation of aldehydes or ketones with compounds containing an active methylene group in the presence of bases, resulting in the formation of ethylene derivatives

12. Reactions: The condensation take place in ammonium hydroxide-ethyl alcohol medium containing ammonium chloride.

13. Reactions: Synthesis of 3- carboxyethylrhodanine by the reactions of carbonyl compounds with various alcohols, hydrogen chloride gas, and the resultant esters purified by vacuum-distillation. The esters were condensed with benzaldehyde , and with isatin in glacial acetic acid.

14. Applications: A rhodanine -based chemo-sensor  RDV proved to be a practical sensor to water sample analysis and cell imaging. Antiviral , anticancer, antimicrobial, and drug discovery. In drug discovery, rhodanines are special heterocyclic structure. Their derivatives possess strong anti-bacterial activity and some of them have shown potent activity against multidrug-resistant pathogens, both under in vitro and in vivo conditions. To treat multi-drug resistant pathogens, the development of novel potent drugs, with superior anti-bacterial efficacy, is most important. One of the promising paths is the design and development of new rhodanine .