Triboronic acid

Tilford et al. synthesized all l-functionalized COF materials with benzene-1,3,5-triboronic acid reacting with l,2,4,5-tetrahydro g benzene substituted by dialkyl, as shown in Figure 6.15. The BET surface area and the pore volume decrease when the all l groups become longer. This work provides a method to modify the pore interior of COFs in order to find promising materials for gas storage. 

Figure 6.15 Synthesis of alkyl-functionalized COFs through condensation of benzene-1,3,5-triboronic acid and 2,6-disubstituted-l,2,4,5- " tetrahydrojiybenzene in tetrahydrofuran (THF) and methanol. ...

The triboronic acid sensors were titrated against four disaccharides lactulose, melibiose, turanose, and trehalose. Across the range of sensors and guests examined, no benefit was found from three (vs two) boronic acid receptor units. For example, the observed stability constant (A obs) of triboronic acid sensor (Ic, 2a) with lactulose was 200 (Figure 6). This value can be contrasted with the value obtained for the analogous diboronic acid (2a derivative) that displayed an observed stability constant (X obs) of... 

Figure 7 Triboronic acid sensors assembled via combinatorial synthesis to evaluate the potential of increased allosteric binding effects through three-point binding (the interchangeable linker units are highlighted in red).

FIGURE 25. Heterodimeric capsules form upon the templated assembly of tris-diol and triboronic acid calixarenes (Reprinted with permission from Ref 57. Copyright 2007 American Chemical Society.)... 

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