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化学进展 2019, Vol. 31 Issue (2/3): 258-274 DOI: 10.7536/PC180631 前一篇   后一篇

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四重氢键自组装体系的设计与应用

裴强**(), 丁爱祥   

  1. 1. 信阳师范学院化学化工学院 信阳 464000
  • 收稿日期:2018-06-28 出版日期:2019-02-15 发布日期:2018-12-20
  • 通讯作者: 裴强
  • 基金资助:
    信阳师范学院博士科研启动基金(18077); 信阳师范学院博士科研启动基金(18072); 河南省高等学校重点科研项目计划(19A150042)

The Design and Application of Quadruple Hydrogen Bonded Systems

Qiang Pei**(), Aixiang Ding   

  1. 1. College of Chemistry and Chemical Engineering, Xinyang Normal University, Xinyang 464000, China
  • Received:2018-06-28 Online:2019-02-15 Published:2018-12-20
  • Contact: Qiang Pei
  • About author:
  • Supported by:
    Doctoral Scientific Research Startup Foundation of Xinyang Normal University(18077); Doctoral Scientific Research Startup Foundation of Xinyang Normal University(18072); Key Scientific Research Project of Henan Provincial Higher Educational Institutions(19A150042)

氢键是自然界中最基本的分子间弱相互作用力之一,是构筑超分子自组装体系的理想推动力。近年来,构筑性能优良的多重氢键组装体系已经成为超分子化学的一个热门研究领域。其中,四重氢键组装体系因具有较强的结合力、合成简单、结构易于修饰以及可预测的识别性能等优点,在构筑超分子组装体方面得到了广泛应用。本文综述了四重氢键组装体系的研究进展,重点介绍了各类四重氢键体系的设计思路及其应用。

Hydrogen bond is one of the most basic weak interaction of natural intermolecular forces and the ideal driving force for constructing supramolecular self-assembly systems. In the past few years, the construction of excellent multiple hydrogen bonded building blocks has become a hot research direction in supramolecular chemistry. Among that, quadruple hydrogen bonded systems are widely used for the construction of supramolecular assemblies due to their several advantages, such as strong binding power, simple synthesis, easily modifiable structure, and predictable recognition performance. In this review, we aim to provide a broad overview of the progress of quadruple hydrogen bonded systems. More specifically, we emphatically elaborate the design principles and applications of various typed quadruple hydrogen bonded systems.

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图1 不同类型的四重氢键组装体系在氯仿中的结合常数(M-1),以及它们之间的次级静电效应(吸引:绿;排斥:红)[3]
Fig. 1 The stability constants(M-1, in CDCl3) of various typed quadruple hydrogen bonded systems and the secondary interactions between them indicated by double headed arrow(attractive: green; repulsive: red)[3]
图2 基于单酰化2, 4-二氨基嘧啶的同源二聚体系[8]
Fig. 2 Homologous dimer based on mono acylated 2, 4-diaminopyrimidines[8]
图3 (a)双酰化的2, 6-二氨基吡啶的稳定构象;(b)双酰化2, 4-二氨基均三嗪的稳定构象及其同源二聚体[9]
Fig. 3 (a) The stable conformation of 2, 6-bis(carbamoyl) pyridine;(b) the stable conformation of 2, 4-bis(carbamoyl)-s-triazines and its homologous dimer[9]
图4 基于三嗪和嘧啶类化合物的DADA·ADAD型同源二聚体及其二聚常数[10]
Fig. 4 The DADA·ADAD typed homologous dimer based on the compounds of s-triazines and pyrimidines and its dimerization constant[10]
图5 (a)基于酰肼喹啉酮单元的同源二聚体;(b)开链化合物9的构象平衡[11]
Fig. 5 (a) Homologous dimer based on hydrazide-quinolinone unit;(b) conformational equilibrium of open chain compound 9[11]
图6 2, 6-二氨基嘌呤的脲基衍生物在溶液中的构象平衡及其同源二聚体[12]
Fig. 6 The conformational equilibrium of ureido derived 2, 6-diaminopurine in solution and its homologous dimer[12]
图7 基化合物11的同源二聚体[13]
Fig. 7 The homologous dimer of compound 11[13]
图8 UPy衍生物在溶液中的异构及二聚体[17]
Fig. 8 Tautomerism and dimerization of UPy derivatives in solution[17]
图9 基于DeAP衍生物的异构及二聚[23]
Fig. 9 Tautomerism and dimerization of DeAP derivatives in solution[23]
图10 抑制质子互变异构体的策略:简并策略 [25]和N-烷基化策略[28]
Fig. 10 The strategy of restraining proton tautomer: degeneration strategy[25] and N-alkylation strategy[28]
图11 基于UN[29] 和UImp[31] 单元的四重氢键二聚体系
Fig. 11 Quadruple hydrogen-bonded dimer based on UN[29] and UImp[31] units
图12 基于1, 3, 5-三嗪-2, 4(1H, 3H)-二酮的脲基衍生物的四重氢键二聚体系[32]
Fig. 12 Quadruple hydrogen-bonded dimer based on the ureido derivatives of 1, 3, 5-triazine-2, 4(1H, 3H)-dione[32]
图13 基于分子内氢键控制构象的线型化合物的四重氢键二聚体系[33]
Fig. 13 Quadruple hydrogen-bonded dimer based on linear compounds with intramolecular hydrogen bonding controlling conformations[33]
图14 基于化合物25a~d的同源二聚体及二聚常数[34]
Fig. 14 The homologous dimer of compounds 25a~d and their dimerization constant[34]
图15 DeAP和DAN之间的DAAD·ADDA型异源二聚体[23]
Fig. 15 The DAAD·ADDA typed heterodimer between DeAP and DAN[23]
图16 UPy和DAN之间的DAAD·ADDA型异源二聚体[37]
Fig. 16 The DAAD·ADDA typed heterodimer between UPy and DAN[37]
图17 基于UG·DAN和DeUG·DAN的DAAD·ADDA型异源二聚体[38, 39]
Fig. 17 The DAAD·ADDA typed heterodimer based on UG·DAN and DeUG·DAN[38, 39]
图18 基于33·34、35·36和37·38的DAAD·ADDA型异源二聚体[41,42,43,44,45]
Fig. 18 The DAAD·ADDA typed heterodimer based on 33·34, 35·36 and 37·38 [41,42,43,44,45]
图19 基于非杂环类酰肼单元的四氢键异二聚体[46, 47]
Fig. 19 Quadruple hydrogen-bonded heterodimer based on the non heterocyclic hydrazide units [46, 47]
图20 末端取代基对酰肼衍生物异二聚体稳定性的影响[48]
Fig. 20 The effect of different terminal substituents on the stability of heterodimer based on the hydrazide derivatives[48]
图21 基于化合物46和47的AADA·DDAD型异二聚体 [49]
Fig. 21 The AADA·DDAD typed heterodimer between compounds 46 and 47[49]
图22 具有AAAA·DDDD四重氢键序列的异源二聚体 [51, 52]
Fig. 22 The heterodimer with AAAA·DDDD quadruple hydrogen bonding sites [51, 52]
图23 基于寡聚芳酰胺的四重氢键分子拉链 [53]
Fig. 23 Quadruple hydrogen-bonded molecular duplexes based on oligoamides [53]
图24 含2, 7-二取代萘环单元的寡聚酰胺构筑的的四重氢键分子拉链 [60]
Fig. 24 Quadruple hydrogen-bonded molecular duplexes constructed by oligoamides containing 2, 7-disubstituted naphthalene units[60]
图25 氢键键合单元被乙炔基团分离的化合物构筑的四重氢键体系 [62,63,64]
Fig. 25 Quadruple hydrogen-bonded system constructed by the compounds with separated hydrogen bond binding units[62,63,64]
图26 (a)2个氢键结合位点集中于同一个原子的化合物构筑四重氢键体系;(b)结构相似的化合物构筑的两重氢键二聚系[65]
Fig. 26 (a) Quadruple hydrogen-bonded system constructed by the compound with an atom bearing two hydrogen bond sites;(b) dual hydrogen-bonded system constructed by the compound with similar structure to compound 62[65]
图27 化合物64对己二酸的分子识别示意图[66]
Fig. 27 The schematic diagram of molecular recognition of adipic acid by compound 64[66]
图28 分子间四重氢键作用对化合物66分子内Diels-Alder反应的诱导[67]
Fig. 28 The intramolecular Diels-Alder reaction of compound 66 induced by intermolecular quadruple hydrogen-bonded action[67]
图29 四重氢键寡聚酰胺模板诱导的烯烃复分解反应 [68]
Fig. 29 The reaction of olefin metathesis induced by template of quadruple hydrogen-bonded oligoamides [68]
图30 四重氢键寡聚酰胺模板诱导的两组二硫键有序交联反应 [70, 71]
Fig. 30 The ordered cross-linking reaction of dual disulfide bond induced by template of quadruple hydrogen-bonded oligoamides[70, 71]
图31 四重氢键寡聚酰胺模板诱导的肽链反平行β-折叠结构[72, 73]
Fig. 31 The antiparallel β-folding structure of peptide induced by template of quadruple hydrogen-bonded oligoamides [72, 73]
图32 四重氢键模板诱导的β-发卡结构[74]
Fig. 32 The β-hairpin structure induced by quadruple hydrogen-bonded template[74]
图33 基于寡聚芳酰胺的多样化凝胶因子[77, 78]
Fig. 33 Versatile gelators based on oligoamides[77, 78]
图34 基于寡聚对苯乙烯修饰的UPy单元的二聚体[79]
Fig. 34 The dimer of UPy unit modified by oligomerization of p-phenylenevinylene[79]
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