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首页> 外文期刊>Chemistry: A European journal >Calix[n]bispyrrolylbenzenes:Synthesis,Characterization,and Preliminary Anion Binding Studies
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Calix[n]bispyrrolylbenzenes:Synthesis,Characterization,and Preliminary Anion Binding Studies

机译：杯[n]双吡咯基苯：合成，表征和初步阴离子结合研究

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摘要

A series of novel calixpyr-role-like macrocycles,calix[n]bis(pyr-rol-2-yl)benzene (calix[n]BPBs,n=2-4) 9a-11a,have been synthesized by means of the TFA-catalyzed condensation reaction of bis(pyrrol-2-yl)benzene 8a with acetone.Calix[2]BPB 9a represents an expanded version of calix[4]-pyrrole in which two of the four meso bridges are replaced by benzene rings.By contrast,systems 10a and 11a,which bear great considerable to calix-bipyrroles 2 and 3,represent higher ho-mologues of the basic calix[n]BPB motif.Solution-phase anion binding studies,carried out by means of ~1H NMR spectroscopic titrations in [D_2]dichloromethane and isothermal ti-tration calorimetry (ITC) in 1,2-di-chloroethane,reveal that 9a binds typical small anions with substantially higher affinities than 1,even though the same number of hydrogen bonding donor groups are found in both compounds.The basic building block for 9a,benzene dipyrrole 8a,also displays a higher affinity for anions than the building block for 1,dimethyldipyrro-methane 16.Structural studies,carried out by single-crystal X-ray diffraction analyses,are consistent with the solution-phase results and reveal that 9a is able to stabilize complexes with chloride and nitrate in the solid state.Structures of the PF_6~- and NO_3~- complexes of 10a were also solved as were those of the acetone adduct of 9a and the ethyl acetate adduct of 11a.
机译：一系列新的杯状杯状大环，杯[n]双（pyr-rol-2-yl）苯（杯[n] BPBs，n = 2-4）9a-11a合成了TFA催化的双（吡咯-2-基）苯8a与丙酮的缩合反应。Calix [2] BPB 9a代表杯的扩展形式，杯形四[4]-吡咯，其中四个内消旋桥中的两个被苯环取代。相比之下，与杯二吡咯2和3相当的系统10a和11a代表基本杯[n] BPB基序的较高同源物。溶液相阴离子结合研究，通过〜1H NMR进行[D_2]二氯甲烷的光谱滴定和1,2-二氯乙烷中的等温滴定量热法（ITC），揭示了9a结合的亲和力比典型的小阴离子高得多，比1更高，尽管9a的基本结构单元，苯二吡咯8a对阴离子的亲和力也比1，dim的结构单元更高乙基二吡咯甲烷16.通过单晶X射线衍射分析进行的结构研究与溶液相结果一致，表明9a能够稳定固态的氯化物和硝酸盐的配合物.PF_6的结构还解析了10a的α-和NO_3-配合物，以及9a的丙酮加合物和11a的乙酸乙酯加合物。

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