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

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

6.7K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
6.7K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.0K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.0K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.1K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.1K
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

6.1K
Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
6.1K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

6.7K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
6.7K
EDTA: Chemistry and Properties01:22

EDTA: Chemistry and Properties

2.4K
Polydentate ligands are most widely used in complexometric titrations because they form more stable complexes with the metal ions than mono- or bidentate ligands due to the chelate effect. Examples of polydentate ligands are ethylenediaminetetraacetic acid (EDTA), crown ethers, and cryptands. The most important feature of optimal polydentate ligands is the ability to form 1:1 complexes in a single-step process. Amino carboxylic acid derivatives are frequently used as complexing agents. EDTA is...
2.4K

You might also read

Related Articles

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

Sort by
Same author

Attaining 19.12% solar cell efficiency for non-fused ring electron acceptors via multi-dimensional charge transport.

Nature communications·2026
Same author

Pyrazine-Based Donor Polymers for Cost-Effective High Performance Organic Solar Cells.

Polymer science & technology (Washington, D.C.)·2026
Same author

Noncovalent Macrocyclic Encapsulation via Terminal "Dynamic Locking" Enabling High-Performance Nonfused Ring Electron Acceptors.

Journal of the American Chemical Society·2026
Same author

Synergistic Passivation and Crystallization Control via a Bifunctional Ionic Liquid for Minimizing Voltage Loss in Wide-Bandgap Perovskites.

Small (Weinheim an der Bergstrasse, Germany)·2026
Same author

One-pot synthesis of quasi-block fluoropolymers for graded heterojunctions via dual resurfacing.

Nature communications·2026
Same author

Vacuum-induced interfacial compaction for scalable fabrication of high-performance organic solar cells.

Nature communications·2026

Related Experiment Video

Updated: Oct 24, 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

6.4K

High-Performance Simple Nonfused Ring Electron Acceptors with Diphenylamino Flanking Groups.

Xiaodong Wang1, Hao Lu1, Jiadong Zhou2

  • 1Beijing Key Laboratory of Energy Conversion and Storage Materials, College of Chemistry, Beijing Normal University, Beijing 100875, China.

ACS Applied Materials & Interfaces
|August 12, 2021
PubMed
Summary

Researchers designed novel nonfused ring electron acceptors using diphenylamine derivatives. The CH-2F acceptor demonstrated superior performance in organic solar cells, achieving a high power conversion efficiency (PCE) of 12.28%.

Keywords:
diphenylamino derivativelow-costmolecular stackingnonfullerene acceptornonfused ring electron acceptor

More Related Videos

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

9.8K
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

9.5K

Related Experiment Videos

Last Updated: Oct 24, 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

6.4K
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

9.8K
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

9.5K

Area of Science:

  • Materials Science
  • Organic Electronics
  • Photovoltaics

Background:

  • Nonfused ring electron acceptors are crucial for organic solar cells (OSCs).
  • Diphenylamine derivatives offer potential for enhancing acceptor properties like solubility and charge transfer.
  • Tuning substituent groups on diphenylamine units significantly impacts acceptor performance.

Purpose of the Study:

  • To design and synthesize novel nonfused ring electron acceptors.
  • To investigate the effect of diphenylamine derivatives on acceptor characteristics.
  • To evaluate the performance of these acceptors in OSC devices.

Main Methods:

  • Synthesis of four nonfused ring electron acceptors (H-2F, CH-2F, OCH-2F, SCH-2F).
  • Characterization of their optical and electronic properties.
  • Fabrication and testing of organic solar cells using these acceptors.
  • Single-crystal X-ray diffraction analysis of CH-2F.

Main Results:

  • Diphenylamine derivatives improved solubility and intramolecular charge transfer.
  • CH-2F exhibited ordered molecular stacking and face-on orientation in blend films.
  • Single-crystal analysis revealed a 2D electron transport network for CH-2F.
  • CH-2F-based OSCs achieved a maximum power conversion efficiency (PCE) of 12.28%.

Conclusions:

  • Triarylamine is a valuable building block for efficient, low-cost nonfused ring electron acceptors.
  • Molecular design, particularly the substituent groups, plays a critical role in OSC performance.
  • CH-2F demonstrates promising potential for high-efficiency organic photovoltaic applications.