論文

査読有り 国際誌
2021年3月1日

A Fluorinated Carbanionic Substituent for Improving Water Solubility and Lipophilicity of Fluorescent Dyes.

Angewandte Chemie (International ed. in English)
  • Hikaru Yanai
  • ,
  • Shoki Hoshikawa
  • ,
  • Yukiko Moriiwa
  • ,
  • Atsushi Shoji
  • ,
  • Akio Yanagida
  • ,
  • Takashi Matsumoto

60
10
開始ページ
5168
終了ページ
5172
記述言語
英語
掲載種別
研究論文(学術雑誌)
DOI
10.1002/anie.202012764

Installation of a carbanionic substituent, that is strongly stabilized by two (trifluoromethyl)sulfonyl (Tf=SO2 CF3 ) groups, into several fluorescence dyes including boron-dipyrromethenes (BODIPYs), fluoresceins, and aminocoumarins has been achieved by the 2,2-bis(triflyl)ethylation reaction of the dye frameworks with highly electrophilic Tf2 C=CH2 , followed by neutralization with NaHCO3 . Despite the contradiction between water solubility and lipophilicity, the carbanion-decorated dyes thus obtained showed significant enhancement of not only water solubility but also lipophilicity. This work clearly demonstrates that the fluorinated, highly stabilized carbanionic substituent is a new option for controlling the macroscopic property of chemical materials.

リンク情報
DOI
https://doi.org/10.1002/anie.202012764
PubMed
https://www.ncbi.nlm.nih.gov/pubmed/33245605
ID情報
  • DOI : 10.1002/anie.202012764
  • PubMed ID : 33245605

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