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Comparative Study
. 2006 Dec 27;128(51):16518-9.
doi: 10.1021/ja067720b.

Diindolylquinoxalines: effective indole-based receptors for phosphate anion

Jonathan L Sessler  1 , Dong-Gyu Cho, Vincent Lynch
Affiliations
Comparative Study

Diindolylquinoxalines: effective indole-based receptors for phosphate anion

Jonathan L Sessler et al. J Am Chem Soc. .

Abstract

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.

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Figures

Scheme 1
Scheme 1
Synthetic Scheme
Figure 1
Figure 1
Evolution of the UV-vis spectrum of receptor 7 (3.99 × 10-5 M in dichloromethane) seen during upon titration with tetrabutylammonium hydrogen phosphate (TBA·H2PO4) (0 to 10 equiv.). (Inset) Job plot for the interaction between receptor 7 and TBA·H2PO4.
Figure 2
Figure 2
Color changes observed upon the addition of anions (10 equiv.) to otherwise identical solutions of receptor 7 (4.34 × 10-5 M in dichloromethane). From left to right; F- + 7, Cl-+ 7, BzO- + 7, HSO4 - + 7, H2PO4 -+ 7, 7.
Figure 3
Figure 3
Single crystal X-ray diffraction structure of receptor 7·TBA·H2PO4. Thermal ellipsoids are scaled to the 50% probability level. Most hydrogen atoms and the TBA cations have been omitted for clarity. (a) View illustrating the two types of phosphate bound receptor 7 complexes found in the solid state structure; (b) view of the (receptor 7·TBA·H2PO4)8 complex seen in the unit cell.
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