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

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
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

3.6K
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...
3.6K
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

6.9K
In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction. 
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
6.9K
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

4.9K
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
4.9K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

4.5K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
4.5K
UV–Vis Spectroscopy: Woodward–Fieser Rules01:29

UV–Vis Spectroscopy: Woodward–Fieser Rules

27.4K
UV–Visible absorption spectra of conjugated dienes arise from the lowest energy π → π* transitions. The light-absorbing part of the molecule is called the chromophore, and the substituents directly attached to the chromophore are called auxochromes. A strong correlation exists between the absorption maxima, λmax, and the structure of a conjugated π system. The Woodward–Fieser rules predict the value of λmax for a given structure by adding the...
27.4K

You might also read

Related Articles

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

Sort by
Same author

Confined Water for Catalysis: Thermodynamic Properties and Reaction Kinetics.

Chemical reviews·2025
Same author

Physics-based prediction of moisture-capture properties of hydrogels.

Nature communications·2024
Same author

Electrolyte Dependence of Li<sup>+</sup> Transport Mechanisms in Small Molecule Solvents from Classical Molecular Dynamics.

The journal of physical chemistry. B·2024
Same author

Examining graph neural networks for crystal structures: Limitations and opportunities for capturing periodicity.

Science advances·2023
Same author

Chemical and Physical Drivers for Improvement in Permeance and Stability of Linker-Free Graphene Oxide Membranes.

Nano letters·2023
Same author

Ultrafine Filteration of Metal Catalysts Enables Fabrication of Silicon Nanowires with Diameter Approaching a Unit Cell Size.

Nano letters·2023

Related Experiment Video

Updated: Dec 5, 2025

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

9.9K

Design Rules for Transparent Push-Pull Electron Acceptors: A Case Study on Perylenediimide Derivatives.

Ki-Jana B Carter1, Jeffrey C Grossman1

  • 1Department of Materials Science and Engineering, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.

The Journal of Physical Chemistry Letters
|October 20, 2020
PubMed
Summary

Researchers modified organic materials to create transparent solar cells. Simple structural changes to perylenediimide acceptors improved transparency and near-infrared absorption, offering new design rules for efficient organic electronics.

More Related Videos

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
11:44

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds

Published on: October 18, 2018

27.2K
Development of Efficient OLEDs from Solution Deposition
07:09

Development of Efficient OLEDs from Solution Deposition

Published on: November 4, 2022

2.6K

Related Experiment Videos

Last Updated: Dec 5, 2025

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

9.9K
Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
11:44

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds

Published on: October 18, 2018

27.2K
Development of Efficient OLEDs from Solution Deposition
07:09

Development of Efficient OLEDs from Solution Deposition

Published on: November 4, 2022

2.6K

Area of Science:

  • Materials Science
  • Organic Electronics
  • Photovoltaics

Background:

  • Transparent photovoltaics are crucial for integrating solar energy into various applications.
  • Systematic tuning of organic materials for transparency remains a challenge.
  • Perylenediimide (PDI) derivatives are promising nonfullerene acceptors.

Purpose of the Study:

  • To investigate the impact of structural modifications on the photoabsorption spectrum of PDI.
  • To establish design principles for achieving transparency and near-infrared absorption in organic solar cells.
  • To explore the use of electron-donating groups and conjugated spacers in PDI-based materials.

Main Methods:

  • Computational screening of electron-donating functional groups with varying strengths.
  • Utilizing relative Mulliken electronegativity as a metric for donor group selection.
  • Synthesizing and characterizing modified PDI molecules with different design motifs.
  • Analyzing photoabsorption spectra to correlate structural changes with optical properties.

Main Results:

  • Electron-donating groups significantly influence the photoabsorption spectrum of PDI.
  • Relative Mulliken electronegativity effectively predicts suitable donor groups.
  • Incorporating conjugated spacers leads to planar molecules with uniform conjugation.
  • Achieved low-energy charge-transfer excitations, enabling near-infrared absorption.
  • Demonstrated the potential for designing transparent, near-infrared absorbing PDI-based electron acceptors.

Conclusions:

  • Simple structural modifications, guided by computational metrics, can effectively tune PDI for transparency.
  • Conjugated spacers are essential for optimizing molecular planarity and electronic properties.
  • The established design rules provide a pathway for developing advanced transparent organic photovoltaic materials.