Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Novel Synthesis of Hydrophilic Dipolar Chromophores using Dendronized Sulfonates

  • Kim, Mi-Rae (Department of Advanced Materials for Information and Display Devices, Pusan National University) ;
  • Maheswara, Muchchintala (Department of Advanced Materials for Information and Display Devices, Pusan National University) ;
  • Do, Jung-Yun (Department of Advanced Materials for Information and Display Devices, Pusan National University)
  • Received : 2010.12.22
  • Accepted : 2011.01.17
  • Published : 2011.02.20
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Abstract

A series of hydrophilic chromophores was synthesized through introduction of dendritic sulfonate anions using click chemistry. A dendron structure bearing several sulfonate groups enhances hydrophilicity of attached chromophores. A click triazole formation connects chromophores with hydrophilic groups. A neutral trichloroethyl sulfonate has versatile features such as easy introduction, chemical endurance for isolation or storage, and convenient transformation to a hydrophilic anion. Zinc and OH mediated cleavage of trichloroethyl group from the neutral sulfonate undergoes to generate a water-soluble sulfonate anion. The solubility was examined with different counter cations and in different pH media and thus increased with the number of attached sulfonate ion. Two hydrophilic chromophores of stilbene-derived and azobenzene-derived dipolar structures exhibit clear negative and positive solvatochromism in protic solvents, respectively.

Keywords

References

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  1. ChemInform Abstract: Novel Synthesis of Hydrophilic Dipolar Chromophores Using Dendronized Sulfonates. vol.42, pp.24, 2011, https://doi.org/10.1002/chin.201124129