The synthesis of sulfide-functionalized (hemi)carceplexes suitable for self-assembly on gold is described. A noncentrosymmetrical carceplex 9 (guest DMF) was synthesized by the combination of calixarene 4 and resorcinarene 3, while a noncentrosymmetrical hemicarceplex 12 (guest NMP) was prepared by the combination of two different resorcinarenes, 3 and 10. These adsorbates form ordered self-assembled monolayers on gold with their quasi C4v axis perpendicular to the surface. The two positions possible for the incarcerated guest lead to diastereotopic surfaces.
|Journal||European journal of organic chemistry|
|Publication status||Published - 2000|
- Cage compounds
Huisman, B-H., Rudkevich, D. M., Farran, A., Verboom, W., van Veggel, F. C. J. M., & Reinhoudt, D. N. (2000). Synthesis of (hemi)carceplex adsorbates for self-assembly on gold. European journal of organic chemistry, 2000(2), 269-274. https://doi.org/10.1002/(SICI)1099-0690(200001)2000:2<269::AID-EJOC269>3.0.CO;2-F