Synthesis and self-assembly of novel oxacalix[2]arene[2]triazine amphiphiles

Abstract

Heteracalixaromatics are an emerging generation of macrocyclic host molecules in supramolecular chemistry. As a typical example of heteracalixaromatics, oxacalix[2]arene[2]triazine adopts a shape-persistent 1,3-alternate conformation and can be easily functionalized. Taking it as a platform, a series of oxacalix[2]arene[2]triazine-based amphiphiles bearing long alkyl chains were synthesized through post-macrocyclization functionalization or 3+1 fragment coupling protocols. The self-assembly behavior of these amphiphiles in a mixture of tetrahydrofuran (THF) and water was investigated. Dynamic light scattering (DLS) measurements revealed that the size of the self-assembled aggregates is dependent on the structure of the amphiphiles. The long alkyl chain substituents and/or intermolecular hydrogen bonds were found to promote the self-assembly.

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Correspondence to Dexian Wang or Meixiang Wang.

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Xu, R., Hou, B., Wang, D. et al. Synthesis and self-assembly of novel oxacalix[2]arene[2]triazine amphiphiles. Sci. China Chem. 59, 1306–1310 (2016). https://doi.org/10.1007/s11426-016-0169-3

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Keywords

  • oxacalix[2]arene[2]triazine
  • heteracalixaromatics
  • amphiphile
  • self-assembly