Related Experiment Video
Updated: Apr 28, 2026
10:39
Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
Published on: August 23, 2018
7.2K
Efficient host-guest energy transfer in polycationic cyclophane-perylene diimide complexes in water
Seán T J Ryan1, Jesús Del Barrio, Indrajit Ghosh
1Melville Laboratory for Polymer Synthesis, Department of Chemistry, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, United Kingdom.
Journal of the American Chemical Society
|June 4, 2014
Summary
Highly charged supramolecular complexes self-assemble in water. These complexes form a 3-polypseudorotaxane with enhanced photophysical properties and act as selective sensors for melatonin.
Area of Science:
- Supramolecular Chemistry
- Materials Science
- Chemical Sensing
Background:
- Cyclic host-guest chemistry is crucial for developing advanced materials.
- Perylene diimides (PDIs) are versatile chromophores with tunable photophysical properties.
- Self-assembly in aqueous media offers environmentally friendly synthetic routes.
Purpose of the Study:
- To investigate the self-assembly of highly charged supramolecular complexes.
- To explore energy transfer (ET) dynamics between host and guest molecules.
- To develop novel supramolecular architectures with enhanced functionalities and sensing capabilities.
Main Methods:
- Synthesis and characterization of ExBox and dicationic PDI derivatives.
- Self-assembly studies in aqueous solutions.
- Spectroscopic techniques (UV-Vis, fluorescence) to monitor complex formation and ET.
- Complexation studies with cucurbit[7]uril (CB[7]) to form polypseudorotaxanes.
- Evaluation of chemosensing capabilities for melatonin.
Main Results:
- Formation of stable hexacationic supramolecular complexes between ExBox and PDIs.
- Observation of efficient energy transfer between ExBox and PDIs.
- Successful self-assembly of a 3-polypseudorotaxane using ExBox, PDIs, and CB[7].
- Significant enhancement of PDI photophysical properties within the polypseudorotaxane structure.
- Demonstration of selective chemosensing for melatonin using the binary complexes.
Conclusions:
- Highly charged supramolecular assemblies can be readily formed in water.
- The 3-polypseudorotaxane architecture leads to superior photophysical properties.
- These supramolecular systems show promise for selective neurotransmitter detection.
Related Concept Videos
02:30Stability of Substituted Cyclohexanes
13.3K
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...
13.3K
01:18Aromatic Hydrocarbon Cations: Structural Overview
3.4K
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...
3.4K
03:13Intermolecular Forces
62.4K
Atoms and molecules interact through bonds (or forces): intramolecular and intermolecular. The forces are electrostatic as they arise from interactions (attractive or repulsive) between charged species (permanent, partial, or temporary charges) and exist with varying strengths between ions, polar, nonpolar, and neutral molecules. The different types of intermolecular forces are ion–dipole, dipole–dipole, hydrogen bonds, and dispersion; among these, dipole–dipole, hydrogen...
62.4K
![[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
8.0K
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.
8.0K
01:28Stability of Conjugated Dienes
3.3K
Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
3.3K
01:17Thermal Electrocyclic Reactions: Stereochemistry
1.6K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
1.6K