A dipodal bis-urea receptor has been synthesized from the reaction of 8-amino quinoline and 1,4-phenylene diisocyanate in dichloromethane, and the anion binding ability of the receptor has been studied using fluoride, chloride, bromide, iodide, perchlorate, nitrate, dihydrogen phosphate and hydrogen sulfate by UV-Vis titrations in DMSO. The results show that the receptor binds each of the anions with a 1:1 stoichiometry, showing high affinity and moderate selectivity for hydrogen sulfate among the anions studied. Ab initio calculations based on density functional theory (DFT) suggest that an anion (X-) is bonded within the cleft formed by the two arms of the receptor through two NH…X- and two aromatic CH…X- interactions. The results from solution and theoretical studies suggest that binding is predominantly influenced by hydrogen bonding interactions and the basicity of anions.
ParkCH, SimmonsHE. (1968) Macrobicyclic amines. III. Encapsulation of halide ions by in, in-1, (k + 2)-diazabicyclo[k.l.m.] alkane-ammonium ions. Journal of the American Chemical Society, 90, 2431–2433.
2.
BellRA, ChristophGG, FronczekFR, MarshRE. (1975) The cation H13O6+: A short, symmetric hydrogen bond. Science, 190, 151–152.
3.
Bowman-JamesK. (2005) Alfred Werner revisited: The coordination chemistry of anions. Accounts of Chemical Research, 38, 671–678.
4.
HossainMA. (2008) Inclusion complexes of halide anions with macrocyclic receptors. Current Organic Chemistry, 12, 1231–1256.
5.
ValiyaveettilS, EngbersenJFJ, VerboomW, ReinhoudtDN. (1993) Synthesis and complexation studies of neutral anion receptors. Angewandte Chemie International Edition, 32, 900–901;
6.
SmithPJ. ReddingtonMV, WilcoxCS. (1992) Ion pair binding by a urea in chloroform solution. Tetrahedron Letters, 33, 6085–6088;
7.
FanE, Van ArmanSA, KincaidS, HamiltonAD. (1993) Molecular recognition: Hydrogen-bonding receptors that function in highly competitive solvents. Journal of the American Chemical Society, 115, 369–370;
8.
InoueY, KanbaraT, YamamotoT. (2003) Preparation of a new receptor for anions, macrocyclic polythiolactam-Structure and high anion-binding ability. Tetrahedron Letters, 44, 5167–5169;
CustelceanR, MoyerBA, HayBP. (2005) A coordinatively saturated sulfate encapsulated in a metal-organic framework functionalized with urea hydrogen-bonding groups. Chemical Communications, 5971–5973.
11.
WuB, LiangJ, YangJ, JiaC, YangX-J, ZhangH, TangbN, JaniakC. (2008) Sulfate ion encapsulation in caged supramolecular structures assembled by second-sphere coordination. Chemical Communications, 1762–1764.
12.
BoiocchiM, Del BocaL, Esteban-GómezD, FabbrizziL, LicchelliM, MonzaniE. (2004) Nature of urea-fluoride interaction: Incipient and definitive proton transfer. Journal of the American Chemical Society, 126, 16507–16514.
13.
CaltagironeC, HiscockJR, HursthouseMB, LightME, GalePA. (2008) 1,3-Diindolylureas and 1,3-diindolylthioureas: anion complexation studies in solution and the solid state. Chemistry - A European Journal, 14, 10236–10243;
14.
PramanikA, ThompsonB, HayesT, TuckerK, PowellDR, BonnesenPV, EllisED, LeeKS, YuH, HossainMA. (2011) Seven-coordinate anion complex with a tren-based urea: Binding discrepancy of hydrogen sulfate in solid and solution states. Organic & Biomolecular Chemistry, 9, 4444–4447.
15.
AlbrechtM, Triyanti SchiffersS, OsetskaO, RaabeG, WielandT, RussoL, RissanenK. (2007) Anion receptors based on a quinoline backbone. European Journal of Organic Chemistry, 2850–2858;
16.
HossainMA, KangSO, PowellD, Bowman-JamesK. (2003) A new class of amide/quaternized amine macrocycles and the chelate effect. Inorganic Chemistry, 42, 1397–1399;
17.
KalitaD, DekaH, SamantaSS, GuchaitS, BaruahJB. (2011) Interactions of amino acids, carboxylic acids, and mineral acids with different quinoline derivatives. Journal of Molecular Structure, 990, 183–196;
18.
MendyJS, SaeedMA, FronczekFR, PowellDR, HossainMA. (2010) Anion recognition and sensing by a new macrocyclic dinuclear copper(II) complex: A selective receptor for iodide. Inorganic Chemistry, 49, 7223–7225.
19.
WongBM. (2009) Noncovalent interactions in supramolecular complexes: A study on corannulene and the double concave buckycatcher. Journal of Computational Chemistry, 30, 51–56;
20.
AmendolaV, BergamaschiG, ButtafavaA, FabbrizziL, MonzaniE. (2010) Recognition and sensing of nucleoside monophosphates by a dicopper(II) cryptate. Journal of the American Chemical Society, 132, 147–156.
