Related Experiment Video
Updated: Jun 24, 2026
10:39
Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
Published on: August 23, 2018
Interfacial supramolecular cyclodextrin-fullerene assemblies: host reorientation and guest stabilization.
Andrea McNally1, Robert J Forster, Tia E Keyes
1National Center for Sensor Research, School of Chemical Sciences, Dublin City University, Dublin 9, Ireland.
Physical Chemistry Chemical Physics : PCCP
|March 18, 2009
Summary
Researchers developed novel self-assembled monolayers using cyclodextrins (CDs) on gold electrodes. Surface-enhanced Raman spectroscopy revealed new carbohydrate signatures sensitive to CD orientation, enabling precise film characterization and fullerene immobilization.
Area of Science:
- Supramolecular chemistry
- Surface science
- Electrochemistry
Background:
- Cyclodextrins (CDs) are widely used in host-guest chemistry.
- Controlling the orientation of self-assembled monolayers (SAMs) is crucial for surface functionalization.
- Electrochemical and spectroscopic methods are key for characterizing surface-bound molecules.
Purpose of the Study:
- To create and characterize self-assembled monolayers of pyridine-substituted cyclodextrins on gold.
- To investigate the orientation of cyclodextrins using Surface-Enhanced Raman Spectroscopy (SERS).
- To immobilize C(60) fullerenes within cyclodextrin monolayers.
Main Methods:
- Self-assembly of cyclodextrin monolayers on polycrystalline gold electrodes.
- Electrochemical characterization of the monolayers.
- Surface-Enhanced Raman Spectroscopy (SERS) for probing molecular orientation and interactions.
- Host-guest complexation for C(60) immobilization.
Main Results:
- Novel SERS signatures between 2100-2300 cm⁻¹ indicative of carbohydrate-gold interactions and CD orientation were observed.
- CD reorientation upon annealing was confirmed by SERS and reversible by alkane thiol backfilling.
- A stable 2:1 cyclodextrin:C(60) trilayer was successfully formed, protecting C(60) from photopolymerization.
Conclusions:
- SERS provides a sensitive tool for determining cyclodextrin orientation on gold surfaces.
- Controlled orientation of cyclodextrin monolayers is achievable and influences subsequent molecular assembly.
- The developed cyclodextrin-fullerene supramolecular system exhibits enhanced stability and defined electrochemical properties.
Related Concept Videos
02:02Chair Conformation of Cyclohexane
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 staggered...
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...
02:30Stability of Substituted Cyclohexanes
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...
![[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2Ffiles%2Fmedia%2Fscience-education%2Fscience-education-thumbs%2F12422.jpg&w=3840&q=75)
01:21[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
01:16Cycloaddition Reactions: MO Requirements for Thermal Activation
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
02:11Conformations of Cyclohexane
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 tetrahedral value,...
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 tetrahedral value,...
![[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2Ffiles%2Fmedia%2Fscience-education%2Fscience-education-thumbs%2F12417.jpg&w=3840&q=75)
01:16[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.