Ein rein organisches Tricarbanion

1,1‐Diamino‐2,2‐bis(triflyl)ethylenes with both twisted and planar structures around the partial “C=C” bond were synthesised. Bonding properties in these compounds were analysed by an experimental approach using high‐resolution X‐ray diffraction data treated with X‐ray wavefunction refinement (XWR). In the twisted compound, a dominant contribution of the charge‐separated resonance structure was revealed. On the contrary, the nearly planar compound still showed π‐bonding character, however, with a considerable contribution of the charge‐separated resonance structure.

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Chemical Bonding in Polarised Push–Pull Ethylenes

Yanai

Suzuki

Kleemiss

et al. 2019

Angewandte Chemie

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

et al. 2021

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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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Chemical Bonding in Polarised Push–Pull Ethylenes

et al. 2019

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1,1-Diamino-2,2-bis(triflyl)ethylenes with both twisted and planar structures around the partial "C = C" bond were synthesised. Bonding properties in these compounds were analysed by an experimental approach using high-resolution X-ray diffraction data treated with X-ray wavefunction refinement (XWR). In the twisted compound, adominant contribution of the charge-separated resonance structure was revealed. On the contrary,t he nearly planar compound still showed pbonding character,h owever,w ith ac onsiderable contribution of the charge-separated resonance structure.

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Ein rein organisches Tricarbanion

Cited by 6 publications

References 27 publications

Chemical Bonding in Polarised Push–Pull Ethylenes

Chemical Bonding in Polarised Push–Pull Ethylenes

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

Chemical Bonding in Polarised Push–Pull Ethylenes

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