CH hydrogen bonding receptors constitute an emerging class of anion sensors and transporters, which, owing to their high proteolytic and pH resistance, are promising for biological applications. CH groups, however, are considered as weak hydrogen bond donors, requiring activation by strongly electron-withdrawing substituents. Accordingly, electron-rich aromatic rings have never been used for this purpose thus far. In this work, we demonstrate that resorcin[4]arenes, well known as π-electron-rich cation receptors, can be converted into CH-bonding anion receptors by simple substitution with four nitro groups. Owing to their unique geometric features, tetranitroresorcin[4]arenes acquire large dipole moments (up to 15.8 D) and highly positive electrostatic potentials at the lower rim, leading to remarkable anion affinities (K_a(Cl⁻) = 1.36 × 10⁵ M⁻¹ in THF). Moreover, we show also that the seemingly innocent alkyl chains surrounding the anion binding site enable high anion transport activities (EC₅₀ down to 0.012 mol%) and resistance to competitive aqueous/organic media.

CH氢键受体构成了一类新兴的阴离子传感器和转运蛋白，由于其高蛋白水解性和pH抗性，在生物应用中具有广阔的前景。然而，CH基团被认为是弱氢键供体，需要通过强吸电子取代基来活化。因此，迄今为止，富电子芳环从未用于此目的。在这项工作中，我们证明间苯二酚[4]芳烃（众所周知的富含π电子的阳离子受体）可以通过用四个硝基进行简单取代而转化为CH键阴离子受体。由于其独特的几何特征，四硝基间苯二酚[4]芳烃在下缘获得大偶极矩（高达15.8 D）和高正静电势，从而导致显着的阴离子亲和力（Ka ₍ Cl ⁻ ) = 1.36 × 10 ⁵ M ^-1（四氢呋喃））。此外，我们还表明，阴离子结合位点周围看似无害的烷基链可实现高阴离子传输活性（EC ₅₀降至 0.012 mol%）和对竞争性水/有机介质的抵抗力。