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

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.8K
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...
2.8K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.4K
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.
2.4K
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

12.0K
Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
12.0K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.9K
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
1.9K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.0K
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.
2.0K
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

3.1K
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...
3.1K

You might also read

Related Articles

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

Sort by
Same author

Silver ion reduction in non-aqueous liquid oligomers with terminal epoxy and amino groups for <i>in situ</i> synthesis of silver nanoparticles.

Nanoscale·2026
Same author

Synthesis and Cytotoxic Activity Study of Conjugates of N-Acyl Derivatives of 3,5-Bis(benzylidene)-4-piperidones and Phenothiazine.

International journal of molecular sciences·2026
Same author

Hexaallylaminocyclotriphosphazene-Modified Dental Compositions for 3D Printing of Dental Crowns.

Polymers·2026
Same author

The Current State of Research in the Field of Photosensitizers and Photoactivators for Photodynamic/Photothermal Cancer Therapy: A Review.

International journal of molecular sciences·2025
Same author

Recent Insights into the Creation of Histone Deacetylase Inhibitors for the Treatment of Human Diseases.

International journal of molecular sciences·2025
Same author

Hydrophobic GeO<sub>2</sub> Aerogels by an Epoxide-Induced Process.

Gels (Basel, Switzerland)·2025
Same journal

RETRACTED: Atta et al. Effect of Montmorillonite Nanogel Composite Fillers on the Protection Performance of Epoxy Coatings on Steel Pipelines. <i>Molecules</i> 2017, <i>22</i>, 905.

Molecules (Basel, Switzerland)·2026
Same journal

Correction: Chen et al. Chemical Composition of <i>Litsea pungens</i> Essential Oil and Its Potential Antioxidant and Antimicrobial Activities. <i>Molecules</i> 2023, <i>28</i>, 6835.

Molecules (Basel, Switzerland)·2026
Same journal

Correction: Ruan et al. Comparison of Extraction, Isolation, Purification, Structural Characterization and Immunomodulatory Activity of Polysaccharides from Two Species of <i>Cistanche</i>. <i>Molecules</i> 2025, <i>30</i>, 4754.

Molecules (Basel, Switzerland)·2026
Same journal

Correction: Li et al. Gastrodin Ameliorates Cognitive Dysfunction in Vascular Dementia Rats by Suppressing Ferroptosis via the Regulation of the Nrf2/Keap1-GPx4 Signaling Pathway. <i>Molecules</i> 2022, <i>27</i>, 6311.

Molecules (Basel, Switzerland)·2026
Same journal

Correction: Zueva et al. Steady-State Kinetics of Enzyme-Catalyzed Hydrolysis of Echothiophate, a P-S Bonded Organophosphorus as Monitored by Spectrofluorimetry. <i>Molecules</i> 2020, <i>25</i>, 1371.

Molecules (Basel, Switzerland)·2026
Same journal

1,4-Diazatriphenylene and Its Hetero-Fused Analogs: Synthesis and Applications.

Molecules (Basel, Switzerland)·2026
See all related articles

Related Experiment Video

Updated: Jul 15, 2025

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
14:07

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Published on: October 3, 2014

13.7K

Hexakis-2-(β-carboxyethenylphenoxy)cyclotriphosphazene: Synthesis, Properties, Modeling Structure.

Pavel Yudaev1, Anastasia Konstantinova1, Vladimir Volkov2

  • 1Mendeleev University of Chemical Technology of Russia, Miusskaya sq., 9, 125047 Moscow, Russia.

Molecules (Basel, Switzerland)
|September 28, 2023
PubMed
Summary
This summary is machine-generated.

Hexakis-2-(β-carboxyethenylphenoxy)cyclotriphosphazene (2-CEPP) was synthesized and characterized. Upon heating, 2-CEPP forms an insoluble, heat-resistant polymer via decarboxylation and polymerization.

Keywords:
heat-resistant polymermodeling structurenanoparticlephosphazenequantum-chemical calculationthermal crystallization

More Related Videos

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

6.3K
The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

12.2K

Related Experiment Videos

Last Updated: Jul 15, 2025

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
14:07

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Published on: October 3, 2014

13.7K
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

6.3K
The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

12.2K

Area of Science:

  • Materials Science
  • Organic Chemistry
  • Polymer Chemistry

Background:

  • Cyclotriphosphazenes are versatile inorganic-organic hybrid compounds with tunable properties.
  • Functionalization of cyclotriphosphazenes can lead to novel materials with specific thermal and chemical behaviors.

Purpose of the Study:

  • To synthesize and characterize a novel cyclotriphosphazene derivative, hexakis-2-(β-carboxyethenylphenoxy)cyclotriphosphazene (2-CEPP).
  • To investigate the thermal behavior and potential applications of 2-CEPP as a precursor for heat-resistant materials.

Main Methods:

  • Synthesis of 2-CEPP via condensation reaction.
  • Structural characterization using NMR spectroscopy (31P, 1H, 13C) and MALDI-TOF mass spectrometry.
  • Quantum-chemical calculations (ab initio, DFT-PBE0/6-311g**) for theoretical estimation of acid strength.
  • Analysis of physical state and phase transitions using small-angle X-ray scattering (SAXS).
  • Thermal analysis including differential-scanning calorimetry (DSC) and solid-state 13C NMR spectroscopy to study thermal decomposition and polymerization.

Main Results:

  • The structure of 2-CEPP was successfully confirmed by spectroscopic and mass spectrometry techniques.
  • Quantum-chemical calculations provided theoretical insights into the acid strength of 2-CEPP.
  • SAXS analysis indicated that 2-CEPP is amorphous but can crystallize upon heating.
  • At 370 °C, 2-CEPP undergoes decarboxylation and polymerization, yielding an insoluble, heat-resistant product.
  • DSC and solid-state 13C NMR confirmed the decarboxylation and polymerization reactions.

Conclusions:

  • 2-CEPP is a novel cyclotriphosphazene derivative with potential as a precursor for high-performance polymers.
  • The thermal decomposition pathway of 2-CEPP involves decarboxylation and polymerization, leading to robust, insoluble materials.
  • This study highlights the potential of functionalized cyclotriphosphazenes in developing advanced heat-resistant polymers.