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A Fluorinated Carbanionic Substituent for Improving Water Solubility and Lipophilicity of Fluorescent Dyes
Author(s) -
Yanai Hikaru,
Hoshikawa Shoki,
Moriiwa Yukiko,
Shoji Atsushi,
Yanagida Akio,
Matsumoto Takashi
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202012764
Subject(s) - lipophilicity , substituent , chemistry , carbanion , solubility , trifluoromethyl , fluorescence , electrophile , sulfonyl , organic chemistry , combinatorial chemistry , photochemistry , medicinal chemistry , catalysis , alkyl , physics , quantum mechanics
Abstract Installation of a carbanionic substituent, that is strongly stabilized by two (trifluoromethyl)sulfonyl (Tf=SO 2 CF 3 ) 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 Tf 2 C=CH 2 , followed by neutralization with NaHCO 3 . 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.