Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.8K
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.
2.8K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.6K
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...
3.6K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.1K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
2.1K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

14.5K
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...
14.5K
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

3.7K
Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
3.7K
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

9.5K
Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
9.5K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Selective Bidentate Coordination Reconstructs Residual PbI<sub>2</sub> to Homogenize Interfacial Energetics in Perovskite Solar Cells.

Journal of the American Chemical Society·2026
Same author

Symmetry-Enabled Optical Spin Initialization of Luminescent Organic Radical Doublet States.

Journal of the American Chemical Society·2026
Same author

How Symmetry Governs the Dihedral Angle Dependence of Intermolecular Spin-Orbit Coupling.

The journal of physical chemistry letters·2026
Same author

Increasing connectivity through self-complementarity enables permanent porosity in a halogen-bonded organic framework.

Chemical science·2026
Same author

The Role of Chirality-Induced Spin Selectivity in Helicene-Based Photogenerated Radical Pairs.

Journal of the American Chemical Society·2026
Same author

Tracking Optical Phonon Dynamics in InP Nanocrystals via Transient Absorption and Femtosecond Stimulated Raman Spectroscopy.

ACS nano·2026

Related Experiment Video

Updated: Dec 25, 2025

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.6K

Cyclophane-Sustained Ultrastable Porphyrins.

Wenqi Liu1, Chenjian Lin1, Jacob A Weber1

  • 1Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States.

Journal of the American Chemical Society
|April 4, 2020
PubMed
Summary
This summary is machine-generated.

This study details the encapsulation of porphyrins within a cyclophane receptor, achieving high binding affinities and significantly enhancing their optical properties and chemical stability for advanced material applications.

More Related Videos

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
14:11

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

6.6K
Synthesis and Characterization of Multi-Modal Phase-Change Porphyrin Droplets
07:59

Synthesis and Characterization of Multi-Modal Phase-Change Porphyrin Droplets

Published on: October 15, 2021

3.9K

Related Experiment Videos

Last Updated: Dec 25, 2025

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.6K
Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
14:11

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

6.6K
Synthesis and Characterization of Multi-Modal Phase-Change Porphyrin Droplets
07:59

Synthesis and Characterization of Multi-Modal Phase-Change Porphyrin Droplets

Published on: October 15, 2021

3.9K

Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Photochemistry

Background:

  • Porphyrins are vital chromophores with applications in catalysis and photomedicine.
  • Controlling porphyrin aggregation and stability in aqueous media remains a challenge.

Purpose of the Study:

  • To develop a cyclophane receptor for encapsulating porphyrins in water.
  • To investigate the impact of encapsulation on porphyrin photophysical properties and chemical stability.

Main Methods:

  • Synthesis of a tricyclic cyclophane receptor.
  • Binding studies of free-base and zinc porphyrins with the receptor in water.
  • Spectroscopic analysis (absorption, emission) of encapsulated porphyrins.
  • Assessment of chemical stability under harsh conditions (acidic, D/H exchange).

Main Results:

  • Subnanomolar binding affinities achieved for porphyrin encapsulation in water.
  • Discovery of two co-conformational isomers due to the receptor's tricyclic structure.
  • Significant enhancement of fluorescence quantum yields and red-shifted optical properties.
  • Unprecedented chemical stability, blocking D/H exchange, protonation, and solvolysis.

Conclusions:

  • Tricyclic cyclophane effectively encapsulates porphyrins, modulating their properties.
  • Encapsulation leads to improved photophysical characteristics and exceptional chemical inertness.
  • Potential applications in advanced materials, artificial photosynthesis, and biomedical devices.