A Fluorescent Quinoline Derivative as Selective Receptor for Fluoride Anions

Abstract

The fluorescent anion receptor 7 based on a quinoline backbone and on amide and urea side chains is prepared and fluorescence titrations in chloroform reveal a high affinity for fluoride (K_a = 14400 M^-1) over chloride (K_a = 3100 M^-1) and bromide (K_a = 640 M^-1).

halides - receptor - quinoline - molecular recognition

References

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Characterization of compound 7: yield 85%. ¹H NMR (400 MHz, CDCl₃): δ = 9.69 (s, NH), 9.23 (s, NH), 8.73 (d, J = 7.7 Hz, 1 H), 7.75 (d, J = 8.5 Hz, 1 H), 7.67 (s, 1 H), 7.49 (t, J = 8.2 Hz, 1 H), 6.37 (s, NH), 3.98 (d, J = 6.6 Hz, 2 H), 3.19 (m, 1 H), 3.03 (m, 1 H), 2.32 (q, J = 6.7 Hz, 2 H), 2.25 (m, 1 H), 1.64 (s, 4 H), 1.39 (m, 4 H), 1.25 (m, 12 H), 1.15 (d, J = 6.6 Hz, 6 H), 1.10 (d, J = 6.9 Hz, 6 H). ¹³C NMR (100 MHz, CDCl₃): δ = 165.0, 163.5, 163.2 (2 × C), 137.4, 136.3, 127.9, 123.5, 121.9, 100.2, 98.4, 76.1, 40.2 (2 × C), 31.6, 31.4, 30.4, 30.2, 29.2, 29.1, 28.2, 26.9, 26.7, 22.5, 22.4, 19.0, 14.0, 13.8. IR (KBr): ν = 3348 (vs), 2928 (vs), 2858 (s), 1646 (s), 1528 (vs), 1460 (m), 1416 (m), 1384 (w), 1360 (m), 1321 (m), 1274 (m), 1224 (m), 1144 (w), 1045 (m), 865 (w), 817 (w), 762 (m), 725 (w), 544 (w) cm^-1. MS (EI, 70 eV): m/z (%) = 498 (7) [M⁺, C₂₉H₄₆N₄O₃ ⁺], 343 (100) [C₂₀H₂₉N₃O₂ ⁺]. Anal. Calcd for C₂₉H₄₆N₄O₃·1/2 H₂O: C, 68.60; H, 9.33; N, 11.04. Found: C, 68.83; H, 9.03; N, 10.90.

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See for comparison:

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<A NAME="RG13605ST-13D">13d</A> See also: Schmidtchen FP. Org. Lett.  2002,  4:  431