Recent Advances in the Synthesis of Ammonium-Based Rotaxanes
Open Access
Abstract
The number of synthetic methods enabling the preparation of ammonium-based rotaxanes has increased very rapidly in the past ten years. The challenge in the synthesis of rotaxanes results from the rather weak interactions between the ammonium-containing rod and the crown ether macrocycle in the pseudorotaxane structure that rely mostly on O•H hydrogen bonds. Indeed, no strong base or polar solvent that could break up H-bonding can be used during the formation of rotaxanes because the two components will separate as two distinct entities. Moreover, most of the reactions have to be performed at room temperature to favor the formation of pseudorotaxane in solution. These non-trivial prerequisites have been taken into account to develop efficient reaction conditions for the preparation of rotaxanes and those are described in detail along this review.Keywords
This publication has 82 references indexed in Scilit:
- A Molecular Cage-Based [2]Rotaxane That Behaves as a Molecular MuscleOrganic Letters, 2008
- Quantitative Active Transport in [2]Rotaxane Using a One-Shot Acylation Reaction toward the Linear Molecular MotorThe Journal of Organic Chemistry, 2008
- Synthesis and Surface Self-Assembly of [3]Rotaxane−Porphyrin Conjugates: Toward the Development of a Supramolecular Surface Tweezer for C60Langmuir, 2008
- Efficient production of [ n ]rotaxanes by using template-directed clipping reactionsProceedings of the National Academy of Sciences, 2007
- SequentialO- andN-Acylation Protocol for High-Yield Preparation and Modification of Rotaxanes: Synthesis, Functionalization, Structure, and Intercomponent Interaction of RotaxanesThe Journal of Organic Chemistry, 2006
- End-capping of Pseudo[2]rotaxane Composed of Alkyl(ferrocenylmethyl)ammonium and Dibenzo[24]crown-8 via Cross Metathesis ReactionsChemistry Letters, 2006
- Operating Molecular ElevatorsJournal of the American Chemical Society, 2006
- Molecular Shuttles by the Protecting Group ApproachThe Journal of Organic Chemistry, 2000
- “Unlock-Lock” Approach to [2] and [3]Rotaxanes: Entering of a Ring through Disulfide Linkage That is Unlocked by Thiol “Key”Chemistry Letters, 2000
- High Yielding and Practical Synthesis of Rotaxanes by Acylative End-Capping Catalyzed by TributylphosphineChemistry Letters, 1999