Oligoether‐Strapped Calix[4]pyrrole: An Ion‐Pair Receptor Displaying Cation‐Dependent Chloride Anion Transport

化学 离子 氟化物 氯化物 高氯酸盐 吡咯 碱金属 无机化学 部分 乙腈 结晶学 有机阴离子 立体化学 有机化学
作者
In‐Won Park,Jaeduk Yoo,Bohyang Kim,Suman Adhikari,Sung Kuk Kim,Yerim Yeon,Cally J. E. Haynes,Jennifer L. Sutton,Christine C. Tong,Vincent M. Lynch,Jonathan L. Sessler,Philip A. Gale,Chang‐Hee Lee
出处
期刊:Chemistry: A European Journal [Wiley]
卷期号:18 (9): 2514-2523 被引量:102
标识
DOI:10.1002/chem.201103239
摘要

Abstract A ditopic ion‐pair receptor ( 1 ), which has tunable cation‐ and anion‐binding sites, has been synthesized and characterized. Spectroscopic analyses provide support for the conclusion that receptor 1 binds fluoride and chloride anions strongly and forms stable 1:1 complexes ([ 1⋅ F] − and [ 1⋅ Cl] − ) with appropriately chosen salts of these anions in acetonitrile. When the anion complexes of 1 were treated with alkali metal ions (Li + , Na + , K + , Cs + , as their perchlorate salts), ion‐dependent interactions were observed that were found to depend on both the choice of added cation and the initially complexed anion. In the case of [ 1⋅ F] − , no appreciable interaction with the K + ion was seen. On the other hand, when this complex was treated with Li + or Na + ions, decomplexation of the bound fluoride anion was observed. In contrast to what was seen with Li + , Na + , K + , treating [ 1⋅F ] − with Cs + ions gave rise to a stable, host‐separated ion‐pair complex, [F ⋅1⋅ Cs], which contains the Cs + ion bound in the cup‐like portion of the calix[4]pyrrole. Different complexation behavior was seen in the case of the chloride complex, [ 1⋅ Cl] − . Here, no appreciable interaction was observed with Na + or K + . In contrast, treating with Li + produces a tight ion‐pair complex, [ 1⋅ Li ⋅ Cl], in which the cation is bound to the crown moiety. In analogy to what was seen for [ 1⋅ F] − , treatment of [ 1⋅ Cl] − with Cs + ions gives rise to a host‐separated ion‐pair complex, [Cl ⋅1⋅ Cs], in which the cation is bound to the cup of the calix[4]pyrrole. As inferred from liposomal model membrane transport studies, system 1 can act as an effective carrier for several chloride anion salts of Group 1 cations, operating through both symport (chloride+cation co‐transport) and antiport (nitrate‐for‐chloride exchange) mechanisms. This transport behavior stands in contrast to what is seen for simple octamethylcalix[4]pyrrole, which acts as an effective carrier for cesium chloride but does not operates through a nitrate‐for‐chloride anion exchange mechanism.
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