Journal
SYNLETT
Volume 27, Issue 14, Pages 2070-2080Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0035-1562469
Keywords
buckybowls; fullerenes; molecular receptors; inclusion complexes; association constants; molecular modelling; supramolecular chemistry
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Funding
- Office of Basic Energy Sciences, Office of Science, U.S. Department of Energy [DE-FG02-04ER15514]
- U.S. Department of Energy (DOE) [DE-FG02-04ER15514] Funding Source: U.S. Department of Energy (DOE)
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This brief review outlines recent developments in synthetic methodologies leading to the preparation of efficient molecular receptors for binding fullerenes via the concave-convex - stacking of the carbon cages with the corannulene pincers. A simple molecular modelling approach allows for a quick a priori assessment of the affinity of the receptor toward fullerenes. NMR titrations and isothermal titration calorimetry provide the association constants of the receptors with fullerenes in solution, and the X-ray crystal structures of the dimeric and trimeric inclusion complexes exhibit the leading structural motif of stacking of the curved-surface carbon networks in these supramolecular associates. 1 Introduction 2 Bis- and Tris-Corannulene Receptors for Fullerenes 2.1 The Synthetic Tools 2.2 Bis-Corannulene Receptors 2.2.1 Corannulene Twin: A Failure 2.2.2 Buckycatcher I: A Breakthrough 2.3 Other Fullerene Receptors with Corannulene Pincers 2.3.1 Polymeric Materials Containing Corannulene Fragments 2.3.2 Bis-Corannulene Clips with Flexible Tethers 2.4 Is Three Better than Two? Increasing the Number of Pincers 2.4.1 Three Corannulene Pincers on a Cyclotriveratrelene Tether 3 Beyond Buckycatcher I: Engineering the Tethers 3.1 Design 3.2 Buckycatcher II 3.3 Bis-Corannulene Receptors Based on Klarner Tethers - Reaching the Affinity Limits 4 Future Directions: Into the Aqueous Phase and on Solid Supports 5 Summary
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