4.4 Article

Synthesis and study of N-acetyl D-glucosamine triazole derivatives as effective low molecular weight gelators

Journal

TETRAHEDRON LETTERS
Volume 56, Issue 23, Pages 3361-3364

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.02.123

Keywords

Hydrogelator; Glucosamine; Triazoles; Self-assembly; Organogels

Funding

  1. Direct For Mathematical & Physical Scien
  2. Division Of Chemistry [1313633] Funding Source: National Science Foundation

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Sugar based low molecular weight gelators have many potential uses for the formation of advanced soft materials. Here we have synthesized a series of peracetylated D-glucosamine triazole derivatives via the Cu catalyzed azide/alkyne cycloaddition reaction (CuAAc) and studied their self-assembling properties in several organic solvents, aqueous solutions, and water. Among the sixteen compounds synthesized and studied, many were able to function as organogelators for multiple solvents. Also seven compounds were able to form hydrogels at low concentrations such as 0.2-1.0 wt %. These indicate that peracetylated D-glucosamine triazole analogs are effective small molecular gelators. (C) 2015 Elsevier Ltd. All rights reserved.

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