• Title/Summary/Keyword: Xanthene structure

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Efficient Cyclization of Substituted Diphenols : Application to the Synthesis of Sulforhodamine B (치환 다이페놀의 효율적 고리화 반응: 설퍼로다민B의 합성에의 응용)

  • Park, Min Kyun;Shim, Jae Jin;Ra, Choon Sup
    • Clean Technology
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    • v.21 no.2
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    • pp.102-107
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    • 2015
  • Rhodamine dyes are widely used as fluorescent probes because of their excellent photophysical properties, such as high extinction coefficients, excellent quantum yields, great photostability, relatively long emission wavelengths. A great synthetic effort has been focused on developing efficient and practical procedures to prepare rhodamine derivatives, because for most applications the probe must be covalently linked to another (bio)molecule or surface. Sulforhodamine B is one of the most used rhodamine dyes for this purpose, because it carries two sulfoxy functions which can be easily utilized for binding with other molecules. Recently, we needed an expedient, practical synthesis of sulforhodamine derivatives. We found the existing procedure for obtaining those compounds unsatisfactory, particularly, with the cyclization process of the dihydroxytriarylmethane (1) to produce the corresponding xanthene derivative (2). We report here our findings, which represent modification of the existing literature procedure and provide access to the corresponding xanthene derivative (2) in a high yield. Use of methanol as a co-solvent was found quite effective to prohibit the water molecule produced during the cyclization reaction from retro-cyclizing back to the starting dihydroxytriarylmethane and the yield of the cyclization was increased (up to 84% from less than 20%). The reaction temperature was significantly lowered (80 vs. 135 ℃). Thus, the reaction proceeds in a higher yield and energy-saving manner where the use of reactants and the production of chemical wastes is minimized.

Synthesis of Novel Fluorescent Dye Based on Fluorescein

  • Hwang, Ji-Yong;Son, Young-A
    • Textile Coloration and Finishing
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    • v.26 no.3
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    • pp.272-276
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    • 2014
  • The functional materials have been developed as a promising research topic toward the end uses for organic materials and applications. In this study, fluorescein based dye was synthesized by three step reaction. We have designed and synthesized the colorimetric dye through the reactions of fluorescein and methoxy group and ethylene diamine and squaric acid. The structure of the non-fluorescent spirolactam was elucidated by $^1H$-NMR, LC-Mass and FT-IR analyzes. Further studies are in progress to understand the effects of various substituent during the recognition process and to develop fluorescein based sensors for cations or anions.