Novel Synthesis of Hydrophilic Dipolar Chromophores using Dendronized Sulfonates

Mi-Rae Kim, Muchchintala Maheswara, Jung-Yun Do
2011 Bulletin of the Korean Chemical Society (Print)  
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
more » ... 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.
doi:10.5012/bkcs.2011.32.2.664 fatcat:wzk6x7iqfjb4hgswfopoisdpdy