In current work, we have prepared a carceplex made of six cavitands, which has a cavity volume of about 900 Å3. This is more than double the volume of trimer carcerand 12, which is also evident by the entrapment of seven molecules of DMSO. The reaction appears to manifest high guest-selectivity in forming the six-cavitand carceplex, and high selectivity in the number of guests as well.
[n]Cavitands and [n]Carceplexes (Christoph Naumann, Samuel Place, and Jianyu Sun)
We have prepared a new series of cavitands that contain more than four resorcinol subunits. These compounds have new symmetry and new cavity size and shape, and thus have the potential to be used to create novel hosts. For example, pentathiol cavitand 13, in DMF in the presence of base and atmospheric oxygen gives carceplex 14o(DMF)2. This is the first carceplex or hemicarceplex linked via disulfide bonds, which opens the door to new chemistry such as reversible or irreversible formation, depending on conditions. Moreover, one can envision a releasing mechanism via reduction of the disulfides. Such release may find application in drug delivery.
Naumann, C.; Roman, E.; Ren, T.; Peinador, C.; Patrick, B.; Kaifer, A. E.; Sherman, J. C. Chem. Eur. J. 2001, 7, 1637.
Naumann, C.; Patrick, B.; Sherman, J. C. J. Am. Chem. Soc. 2001, in press.