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Progress in Chemistry 2020, Vol. 32 Issue (11): 1665-1679 DOI: 10.7536/PC200530 Previous Articles   Next Articles

Macromolecular and Supramolecular Helical Tubes: Synthesis and Functions

Dan-Wei Zhang1,**(), Hui Wang1, Zhan-Ting Li1,**()   

  1. 1. Department of Chemistry, Fudan University, Shanghai 200438, China
  • Received: Revised: Online: Published:
  • Contact: Dan-Wei Zhang, Zhan-Ting Li
  • Supported by:
    the National Natural Science Foundation of China(21772026)
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It has been established that hydrophobicity, hydrogen bonding, electrostatic attraction, halogen bonding and coordination all can be utilized to stabilize the folding and/or helicity of aromatic macromolecules and supramolecular systems. The resulting aromatic helical tubes possess defined diameters and tunable depth and can be used as synthetic receptors for recognizing or encapsulating a variety of guest species, achieving chirality induction and transfer, promoting organic transformations, and as artificial channels for transmembrane transport. This review highlights the advance in the construction of such family of macromolecular and supramolecular tubes from aromatic segments and their important functions. In the first section, we introduce the background of the formation of tubular structures from different strategies and the features of the supramolecular and macromolecular approaches. We then highlight the formation of molecular tubes from various oligomeric molecules with aromatic amide, hydrazide, triazole and ethyne repeat segments. In the following section, we describe the use of polymeric backbones with the above repeat segments. The self-assembly strategy for the formation of supramolecular tubes is then summarized in another section. In particular, the utility of hydrogen bonding, halogen bonding and coordination interactions has been described. When available, the functions of the tubular structures are briefly presented. In the last section, we discuss the synthetic challenges for the formation of long macromolecular tubes and the new potential applications of this family of structurally unique structures.

Contents

1 Introduction

2 Aromatic oligomeric tubes

2.1 Aromatic amide and hydrazide backbones

2.2 Aromatic triazole backbones

2.3 Aromatic ethyne backbones

3 Aromatic polymeric tubes

3.1 Aromatic amide backbones and analogues

3.2 Aromatic triazole and oxadiazole backbones

3.3 Aromatic ethyne backbones

4 Aromatic supramolecular tubes

5 Conclusion and outlook

Key words: helical tubes, aromatic foldamers, non-covalent interactions, molecular recognition, transmembrane transport
Fig.1 The crystal structure of oligomer 7[34]
Fig.2 The crystal structure of oligomer 8[35]
Fig.3 Schematic representation of solvophobically driven folding-inducing-folding of oligomers 11,(R)-12 and 13[53]
Scheme 1 The synthesis of polymers P25~P27
Fig.4 (a) Side and (b) top view of optimized right-handed helix formed by polymer P29a of 9 turns with a cavity diameter of 1.3 nm. The tetra(ethylene glycol) chains were replaced with methyl groups for clarity[71]
Fig.5 Schematic presentation of the transmembrane channel formed by helical polymer P30[74]
Fig.6 Calculated helix of polymers P34 and P35, highlighting a large cavity diameter[82]
Scheme 2 The synthesis of polymers P41 and P42[86]
Scheme 3 Pyridine-Pd2+ binding of 48a~c forms metal-ligand complexes to generate coordination supramolecular helical polymer or π-stacked columnar polymer[93]
Fig.7 Crystal structure of 53a·MeOH[98]
Fig.8 Crystal structure of 53b·H2O[99]
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