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. Water solubility (and aqueous solubility) is a key macroscopic property for chemical materials directed towards biorelevant applications. [1] The most common way to improve the water solubility of less soluble compounds is introduction of ionic groups such as the sulfonato group into the molecular structure (Figure 1 A). However, such ionic functionalities
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