Diindolylquinoxalines: effective indole-based receptors for phosphate anion.
The synthesis of a new series of 2,3-diindol-3'yl quinoxalines (DIQ), as well as a comparison of their anion recognition properties to those of our previously reported pyrrole based sensors, 2,3-dipyrrol-2'yl quinoxalines, is reported. To the best of our knowledge, this new DIQ system represents the first example of a free-standing indole-based small molecule receptor for which evidence of anion binding is available both in solution and in the solid-state. It also provides one of the few structurally characterized neutral receptor-dihydrogen phosphate complexes. This work thus serves to demonstrate the utility of indoles as an anion recognition motif.
Sessler
Jonathan L
JL
Department of Chemistry and Biochemistry, Institute for Cellular and Molecular Biology, The University of Texas at Austin, 1 University Station A5300, Austin, TX 78712-0156, USA. sessler@mail.utexas.edu
Cho
Dong-Gyu
DG
Lynch
Vincent
V
D000838:Anions / Q000737:chemistry; D001665:Binding Sites; D018360:Crystallography, X-Ray; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010710:Phosphates / Q000737:chemistry*; D011810:Quinoxalines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000838:Anions; D007211:Indoles; D010710:Phosphates; D011810:Quinoxalines