寡聚芳酰胺类受体在分子识别方面的研究进展
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摘要
寡聚芳酰胺是一类以芳环为构筑单元、酰胺键链接的稳定化合物,因含有氢的供体和受体使它对客体分子表现出特殊的识别能力,目前已成为国内外研究的热点领域之一。结合近年来国内外相关文献,首先综述了寡聚芳酰胺受体高效识别有机分子的研究进展,目前认为它主要通过氢键来识别醇类、胺类以及糖类等客体分子,并可通过修饰受体分子来提高选择性识别客体的能力;其次介绍了该受体识别无机分子的研究现状,当前研究较多客体分子包括富勒烯、水分子、肼、双氧水等,π-π共轭和氢键是该受体主要识别作用力;然后分别综述了该类受体分子在识别阳离子和阴离子方面的进展,前者包括有机阳离子、碱金属以及过渡金属,识别它们的主要作用力有配位键和氢键,后者包括无机阴离子和有机阴离子,识别它们的是电荷中性偶极作用力。然而,该类受体在制备和识别环境方面存在着不足,制备功能特定、性能稳定的寡聚芳酰胺受体分子是未来发展方向。
Aromatic oligoamide compounds are a class of aromatic ring as building units,the link of amide bond stable compounds,due to exhibiting special recognition ability to guest molecules by containing hydrogen donor and receptor,now they has become one of hot research fields in the world.In this review,according to the related papers at home and abroad in recent years,firstly we summarized the recent progress in molecular recognition of aromatic oligoamide compounds as synthetic receptors to organic molecules,the viewpoint that the guests molecules containing alcohol,amine and sugar were recognized by hydrogen bonding was accepted at present,and the selectivity recognition ability can be enhanced by modified receptors.Secondly,their current situation in molecular recognition to inorganic molecules was introduced,fullerene,water molecule,hydrazinium,hydrogen peroxide as guest molecules were researched frequently,which were recognized byπ-πinteraction and hydrogen bonding.Next,the recent progress of the receptors in molecular recognition to cation and anion were summarized,the former mainly contained organic cation,alkali metal and transition metal,which were recognized by coordination and hydrogen bonding.The latter contained inorganic anion and organic anion,which were recognized by charge-neutral dipoles.However,this kind of receptor molecules existing the shortcomings in synthesis and recognition condition fields were mentioned,and the receptors with given function and well stability will develop trends in the future.
Aromatic oligoamide compounds are a class of aromatic ring as building units,the link of amide bond stable compounds,due to exhibiting special recognition ability to guest molecules by containing hydrogen donor and receptor,now they has become one of hot research fields in the world.In this review,according to the related papers at home and abroad in recent years,firstly we summarized the recent progress in molecular recognition of aromatic oligoamide compounds as synthetic receptors to organic molecules,the viewpoint that the guests molecules containing alcohol,amine and sugar were recognized by hydrogen bonding was accepted at present,and the selectivity recognition ability can be enhanced by modified receptors.Secondly,their current situation in molecular recognition to inorganic molecules was introduced,fullerene,water molecule,hydrazinium,hydrogen peroxide as guest molecules were researched frequently,which were recognized byπ-πinteraction and hydrogen bonding.Next,the recent progress of the receptors in molecular recognition to cation and anion were summarized,the former mainly contained organic cation,alkali metal and transition metal,which were recognized by coordination and hydrogen bonding.The latter contained inorganic anion and organic anion,which were recognized by charge-neutral dipoles.However,this kind of receptor molecules existing the shortcomings in synthesis and recognition condition fields were mentioned,and the receptors with given function and well stability will develop trends in the future.
引文
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[15]Gong B.Hollow crescents,helices,and macrocycles from enforced folding and folding-assisted macrocyclization[J].Accounts of Chemical Research,2008,41(10):1376-1386.
[16]杨永安,冯文,袁立华.环芳酰胺的合成及自组装行为[J].高等学校化学学报,2011,32(9):1950-1961.Yang Y A,Feng W,Y L H.Synthesis of cycloaramides and self-assembly behaviors[J].Chemical Journal of Chinese Universities,2011,32(9):1950-1961.
[17]He Y Z,Xu M,Gao R Z,et al.Two-component supramolecular gels derived from amphiphilic shape-persistent cyclo[6]aramides for specific recognition of native arginine[J].Angewandte Chemie International Edition,2014,126(44):12028-12033.
[18]杨永安,袁立华,胡晋川,等.带极性侧链的环[6]芳酰胺的球形自组装[J].物理化学学报,2010,26(6):1557-1564.Yang Y A,Yuan L H,Hu J C,et al.Spherical assemblies of a cyclo[6]aramide with polar side chains[J].Acta Physico-Chimica Sinica,2010,26(6):1557-1564.
[19]Yuan L H,Feng W,Yamato K,et al.Highly efficient,onestep macrocyclizations assisted by the folding and preorganization of precursor oligomers[J].Journal of the American Chemical Society 2004,126(36):11120-11121.
[20]Feng W,Yamato K,Yang L Q,et al.Efficient kinetic macrocyclization[J].Journal of the American Chemical Society2009,131(7):2629-2637.
[21]Sanford A R,Yuan L H,Feng W,et al.Cyclic aromatic oligoamides as highly selective receptors for the guanidinium ion[J].Chemical Communication,2005,37(37):4720-4722.
[22]Yamato K,Yuan L H,Feng W,et al.Crescent oligoamides as hosts:conformation-dependent binding specificity[J].Organic&Biomolecular Chemistry,2009,7(18):3643-3647.
[23]Yang Y A,Feng W,Hu J C,et al.Strong aggregation and directional assembly of aromatic oligoamide macrocycles[J].Journal of the American Chemical Society,2011,133(46):18590-18593.
[24]Brooks S J,Gale P A,Light M E.Anion-binding modes in a macrocyclic amidourea[J].Chemical Communication,2006,41(41):4344-4346.
[25]Abe H,Chida Y,Kurokawa H,et al.Selective binding of D2h-symmetrical,acetylenelinked pyridine/pyridone macrocycles to maltoside[J].Journal of Organic Chemistry,2011,76(9):3366-3371.
[26]H?ger S,Meckenstock A.D.Template-directed synthesis of shape persistent macrocyclic amphiphiles with convergently arranged functionalities[J].Chemistry-A European Journal,1999,5(6):1686-1691.
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[28]Wu X X,Liu R,Gong B,et al.Discrete stacking of aromatic oligoamide macrocycles[J].Journal of the American Chemical Society,2015,137(18):5879-5882.
[29]Shao X B,Yi H P.Hydrogen bonding mediated oligobenzamide foldamer receptors that efficiently bind a triol and saccharides in chloroform[J].New Journal of Chemistry,2005,29(9):1213-1218.
[30]Hou J L,Shao X B,Chen G J,et al.Hydrogen bonded oligohydrazide foldamers and their recognition for saccharides[J].Journal of the American Chemical Society,2004,126(39):12386-12394.
[31]Li C,Wang G T,Yi H P,et al.Diastereomeric recognition of chiral foldamer receptors for chiral glucoses[J].Organic Letters,2007,9(9):1797-1800.
[32]Ong W Q,Zhao H Q,Sun C,et al.Patterned recognitions of amines and ammonium ions by apyridine-based helical oligoamide host[J].Chemical Communication,2012,48(51):6343-6345.
[33]Bao C,Kauffmann B,Gan Q,et al.Converting sequences of aromatic amino acid monomers into functional three-dimensional structures:second-generation helical capsules[J].Angewandte Chemie,2008,120(22):4221-4224.
[34]Bao C,Gan Q,Kauffmann B,et al.A self-assembled foldamer capsule:combining single and double helical segments in one aromatic amide sequence[J].Chemistry-A European Journal,2009,15(43):11530-11536.
[35]Ferrand Y,Kendhale A M,Kauffmann B,et al.Diastereoselective encapsulation of tartaric acid by a helical aromatic oligoamide[J].Journal of the American Chemical Society,2010,132(23):7858-7859.
[36]Zhang C X,Wang Q,Long H,et al.A highly C70selective shape-persistent rectangular prism constructed through one-step alkyne metathesis[J].Journal of the American Chemical Society 2011,133(51):20995-21001.
[37]Yanagisawa M,Tashiro K,Yamasaki M,et al.Hosting fullerenes by dynamic bond formation with an iridium porphyrin cyclic dimer:a“chemical friction”for rotary guest motions[J].Journal of the American Chemical Society,2007,129(39):11912-11913.
[38]Gil-Ramirez G,Karlen S D,Shundo A,et al.A cyclic porphyrin trimer as a receptor for fullerenes[J].Organic Letters,2010,12(15):3544-3547.
[39]Furuyama T,Ogura Y,Yoza K,et al.Superazaporphyrins:meso-pentaazapentaphyrins and one of their low-symmetry derivatives[J].Angewandte Chemie,2012,124(44):11272-11276.
[40]Zhang C X,Long H,zhang W.A C84selective porphyrin macrocycle with an adaptable cavity constructed through alkyne metathesis[J].Chemical Communication,2012,48(48):6172-6174.
[41]Zhu Y Y,Li C,Li G Y,et al.Hydrogen-bonded aryl amide macrocycles:synthesis,single-crystal structures,and stacking interactions with fullerenes and coronene[J].Journal of Organic Chemistry,2008,73(5):1745-1751.
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