ORGN 344

Host molecule 1 dimerizes in water to form a well-defined nano-capsule; a supramolecular event that can trap guests as large as steroids,¹ bring about the separation of hydrocarbon gases,² and engender a nano-scale reaction flask for novel photochemical conversions.³ With this disparate range of properties in mind, we are interested in forming different nano-capsules that also assemble via the hydrophobic effect.  By way of example, we will report on our progress in the synthesis of deep-cavity cavitand 2, a host that is expected to dimerize in aqueous solution to form capsules with an internal volume of ca. 3 nm in length and ca. 1 nm at its widest point.

References

1.   Gibb, C. L. D., Gibb, B. C., J. Am. Chem. Soc., 2004, 126, 11408-11409.

2.   Gibb, C. L. D., Gibb, B. C., J. Am. Chem. Soc., 2006, 128, 16498-16499.

3.   Natarajan, A.; Kaanumalle, L. S.; Jockusch, S.; Gibb, C. L. D.; Gibb, B. C.; Turro, N. J. and Ramamurthy, V. J. Am. Chem. Soc., 2007, 129, 4132-4133.