Simple isophthalamides/dipicolineamides as active transmembrane anion transporters

ABSTRACT

Eight N,N´-diarylisophthalamide/dipicolineamide derivatives have been synthesised and fully characterised, both in solution and in the solid state. The transmembrane anion transport properties of these compounds have been studied by chloride-selective electrode and fluorescence experiments. The substitution pattern of the aromatic moieties determines the transport properties of these systems, with those containing electron-withdrawing groups in their structures being the most active ones of the series.

Graphical abstract

KEYWORDS:

• Anion binding
• anion transport
• ion-selective electrode
• liposomes

Disclosure statement

No potential conflict of interest was reported by the authors.

Note

Three dimensional X-ray data for L3 were collected on a BRUKER SMART APEX CCD diffractometer. Complex scattering factors were taken from the program SHELXL-2016 (29) running under the WinGX program system (30) as implemented on a Pentium® computer. The structure was solved with SIR92 (31) and refined by full-matrix least-squares on F². All hydrogen atoms, except those corresponding to the N-H fragments of the amide groups, which were refined freely in the final stages of refinement, were included in calculated positions and refined in riding mode. Refinement converged with anisotropic displacement parameters for all non-hydrogen atoms.

Crystal data for receptor L3: C₂₀H₁₄Cl₂N₂O₂; molecular weight = 385.23 g·mol⁻¹; crystal system: monoclinic; space group: P 2₁/c; T = 298(2) K; a = 36.809(5) Å; b = 5.0601(7) Å; c = 9.7506(13) Å; α = 90º; β = 95.567(2)º; γ = 90º; V = 1807.5(4) ų; F(000) = 792; Z = 4; λ (MoK_α) = 0.71073 Å; D_calc = 1.416 g·cm⁻³; μ = 0.376 mm⁻¹. GOF = 0.945; 19218 reflections measured (2.22 ≤ Θ ≤ 27.99), of which 4093 were unique (R_int: 0.1635), used in all calculations. The final R₁ was 0.0540 (I > 2σ(I)) and wR₂ was 0.1375 (all data). CCDC 1961241.

Supplementary material

Supplemental data for this article can be accessed here.

Additional information

Funding

Funding from Consejería de Educación de la Junta de Castilla y León (project BU075G19) is gratefully acknowledged. Financial support from MIUR (PRIN 2017 project 2017EKCS35) is gratefully acknowledged by G.P. and C.C