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

2.4K
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
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
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

1.8K
Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
1.8K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.6K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.6K
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

8.4K
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...
8.4K

You might also read

Related Articles

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

Sort by
Same author

Development of Intramolecular Charge Transfer-Type NIR Fluorescent Dyes Bearing a Pyrazino[2,3-b]quinoxaline-Based Electron Acceptor.

Chemistry, an Asian journal·2026
Same author

Synthesis, Structures, and Properties of λ<sup>5</sup>-Phosphinine Functionalized with <i>p</i>-Benzoquinone.

The Journal of organic chemistry·2026
Same author

Enzyme-Directed Assembly of Antiparallel Cellulose II Nanocrystals: Unraveling the Mechanism Beyond Spontaneous Crystallization.

JACS Au·2026
Same author

A Precisely Bromo-Functionalized [9]Cycloparaphenylene as a Platform for Late-Stage Multisite π-Extension Toward Chiral Nanohoops.

Angewandte Chemie (International ed. in English)·2025
Same author

Biosynthesis and Export of Membrane-Enveloped Selenium Nanoparticles by <i>Escherichia coli</i>.

Environmental science & technology·2025
Same author

In-situ synchrotron SAXS/WAXD analysis for tracking the change in multiscale structure of wood during macroscopic flexural deformation.

Carbohydrate polymers·2025

Related Experiment Video

Updated: Jul 16, 2025

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

6.2K

Intramolecular Electron Transfer in Multi-Redox Systems Based on Cyclic [3]Spirobifluorenylene Compound.

Tomoya Imai1, Daisuke Sakamaki2, Shinobu Aoyagi1

  • 1Department of Information and Basic Science, Graduate School of Science, Nagoya City University, 1 Yamanohata, Mizuho-cho, Mizuho-ku, Nagoya, Aichi, 467-8501, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 23, 2023
PubMed
Summary

This study synthesized a novel spirobifluorenylene molecule to explore electron transfer in orthogonal π-conjugated systems. Spiro-conjugation facilitates efficient intramolecular electron transfer, showing promise for molecular wire applications.

Keywords:
areneselectron transfermacrocyclesredox chemistryspiro compounds

More Related Videos

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
07:07

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

Published on: March 12, 2015

9.7K
Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
08:51

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Published on: October 24, 2017

9.6K

Related Experiment Videos

Last Updated: Jul 16, 2025

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

6.2K
Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
07:07

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

Published on: March 12, 2015

9.7K
Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
08:51

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Published on: October 24, 2017

9.6K

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Physical Chemistry

Background:

  • Investigating electron transfer in π-conjugated systems is crucial for developing advanced molecular materials.
  • Orthogonal π-conjugated chains present unique challenges and opportunities for charge transport.

Purpose of the Study:

  • To design and synthesize a cyclic [3]spirobifluorenylene molecule with bulky alkyl groups.
  • To investigate intramolecular electron transfer phenomena in a π-conjugated system with orthogonal chains.

Main Methods:

  • Synthesis of cyclic [3]spirobifluorenylene (1).
  • Characterization using absorption and fluorescence spectroscopy, electrochemical analysis, TD-DFT calculations, NTO calculations, and ESR spectroscopy.
  • Chemical oxidation using SbCl5.

Main Results:

  • Spiro-conjugation led to splitting of HOMO levels and a small SOMO-HOMO gap, facilitating intramolecular electron transfer.
  • Electrochemical oxidation revealed interchain Coulombic repulsion.
  • TD-DFT and NTO calculations visualized geometry-featured interchain electronic transitions.
  • NIR absorption band exceeding 2000 nm attributed to intramolecular electron transfer.
  • ESR experiments confirmed spin delocalization via hole hopping.

Conclusions:

  • Spiro-conjugation is effective in bridging orthogonal π-conjugated units.
  • This approach facilitates smooth intramolecular electron transfer, demonstrating potential for molecular wire applications.