Related Experiment Video
Updated: Mar 30, 2026
09:44
Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
Published on: October 15, 2019
13.1K
Synthesis and Structural Characterization of a Cyclen-Derived Molecular Cage
Alexander Ganss1, Raquel Belda2, Javier Pitarch2
1Fachbereich Chemie - Organische Chemie, Technische Universität Kaiserslautern , Erwin-Schrödinger-Straße, 67663 Kaiserslautern, Germany.
Organic Letters
|November 18, 2015
Summary
Researchers created a novel molecular cage from a tetrafunctionalized cyclen derivative. This cage efficiently forms dimetallic copper(II) complexes, paving the way for new cascade complexes with anions.
Area of Science:
- Supramolecular Chemistry
- Coordination Chemistry
- Organic Synthesis
Background:
- Cyclen derivatives are versatile macrocyclic platforms.
- Molecular cages offer unique host-guest properties.
- Metal complexes with macrocycles are crucial in catalysis and medicine.
Purpose of the Study:
- To synthesize a novel bis(cyclen)-derived molecular cage.
- To investigate the coordination behavior of the cage with metal ions.
- To explore the potential of these complexes in forming new supramolecular structures.
Main Methods:
- Multi-step organic synthesis involving functionalized cyclen derivatives and diamines.
- Reductive amination and demetalation steps for cage formation.
- Potentiometric titrations for metal-ligand binding studies.
- X-ray crystallography for structural elucidation of metal complexes.
Main Results:
- High-efficiency synthesis of a bis(cyclen)-derived molecular cage.
- Formation of stable dimetallic copper(II) complexes with selective coordination to cyclen units.
- Structural evidence suggesting the potential for anion incorporation between metal centers.
Conclusions:
- The synthesized molecular cage is a robust platform for constructing dimetallic complexes.
- The selective coordination of copper(II) ions highlights the precise control offered by the cage structure.
- These findings open avenues for designing novel supramolecular architectures and functional materials.
More Related Videos
Related Concept Videos
01:18Aromatic Hydrocarbon Cations: Structural Overview
4.3K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
Removing one hydrogen from the intervening CH2 group...
4.3K
02:33Stereoisomerism of Cyclic Compounds
11.9K
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
11.9K
02:30Stability of Substituted Cyclohexanes
17.3K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
17.3K
02:11Conformations of Cyclohexane
17.3K
Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
17.3K
02:02Chair Conformation of Cyclohexane
21.4K
The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
21.4K
01:26Thermal and Photochemical Electrocyclic Reactions: Overview
3.2K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
3.2K