4.4 Article

Synthesis, structure, and host-guest properties of an anthracene-based macrocyclic arene

Journal

TETRAHEDRON LETTERS
Volume 59, Issue 8, Pages 730-733

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2018.01.017

Keywords

Molecular recognition; New macrocycles; New hosts; Macrocyclic arenes; Host-guest properties

Funding

  1. National Natural Science Foundation of China [21402162, 21772118]
  2. Shanghai Pujiang Program of the Shanghai Education Development Foundation [16PJD024]
  3. Shuguang Program of the Shanghai Education Development Foundation
  4. Shanghai Municipal Education Commission

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A new anthracene-based macrocyclic host (H) was designed and synthesized. H has a molecular box-type structure with a flexible cavity. It exhibits highly strong binding affinities towards selected cationic model guests, butyl viologen (BV), dibutylammonium (DBA), and octyltrimethylammonium (OTMA). For example, the association constant of H and BV is up to (2.2 +/- 0.3) x 10(7) M-1; it is interesting to observe host-guest charge-transfer band (and color change) and fluorescence quenching of H's anthracene unit due to the formation of inclusion complex. (C) 2018 Elsevier Ltd. All rights reserved.

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