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

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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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Authors and Affiliations

  1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China

    Ruibin Xu, Baoyong Hou & Dexian Wang

  2. The Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, 100084, China

    Meixiang Wang

  3. University of Chinese Academy of Sciences, Beijing, 100049, China

    Ruibin Xu & Dexian Wang

Authors
  1. Ruibin Xu
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  2. Baoyong Hou
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  3. Dexian Wang
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  4. Meixiang Wang
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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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  • DOI: https://doi.org/10.1007/s11426-016-0169-3

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