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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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.
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

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, the...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

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Related Experiment Video

Updated: May 25, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
12:07

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

Modulating dye E(S+/S*) with efficient heterocyclic nitrogen containing acceptors for DSCs.

Jared H Delcamp1, Aswani Yella, Mohammad K Nazeeruddin

  • 1Laboratory for Photonics and Interfaces, Institution of Chemical Sciences and Engineering, School of Basic Sciences, Swiss Federal Institute of Technology, CH-1015 Lausanne, Switzerland. jared.delcamp@epfl.ch

Chemical Communications (Cambridge, England)
|January 21, 2012
PubMed
Summary

New nitrogen-containing heterocycles were synthesized for dye-sensitized solar cells (DSCs). These novel materials allow for tuning of the excited-state oxidation potential with minimal impact on the ground-state oxidation potential.

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Vibrational Spectra of a N719-Chromophore/Titania Interface from Empirical-Potential Molecular-Dynamics Simulation, Solvated by a Room Temperature Ionic Liquid
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Integrating a Triplet-triplet Annihilation Up-conversion System to Enhance Dye-sensitized Solar Cell Response to Sub-bandgap Light
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Vibrational Spectra of a N719-Chromophore/Titania Interface from Empirical-Potential Molecular-Dynamics Simulation, Solvated by a Room Temperature Ionic Liquid
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Integrating a Triplet-triplet Annihilation Up-conversion System to Enhance Dye-sensitized Solar Cell Response to Sub-bandgap Light
11:26

Integrating a Triplet-triplet Annihilation Up-conversion System to Enhance Dye-sensitized Solar Cell Response to Sub-bandgap Light

Published on: September 12, 2014

Area of Science:

  • Materials Science
  • Electrochemistry
  • Photovoltaics

Background:

  • Dye-sensitized solar cells (DSCs) are a promising photovoltaic technology.
  • Tuning the electronic properties of dyes is crucial for optimizing DSC performance.
  • Nitrogen-containing heterocycles are versatile building blocks for functional materials.

Purpose of the Study:

  • To synthesize novel acceptor motifs based on nitrogen-containing heterocycles for DSC applications.
  • To investigate the effect of nitrogen atom incorporation and extended conjugation on dye properties.
  • To achieve precise control over the excited-state oxidation potential of dyes.

Main Methods:

  • Synthesis of nitrogen-containing heterocyclic compounds.
  • Spectroscopic and electrochemical characterization of the synthesized dyes.
  • Evaluation of dye performance in dye-sensitized solar cells.

Main Results:

  • Successfully synthesized novel acceptor motifs based on nitrogen-containing heterocycles.
  • Demonstrated that selective addition of nitrogen atoms and increased conjugation effectively tune the excited-state oxidation potential (E((S+/S*))).
  • Showed minimal perturbation of the ground-state oxidation potential (E((S+/S))) during tuning.

Conclusions:

  • The developed nitrogen-containing heterocyclic acceptor motifs offer a viable strategy for optimizing dye properties in DSCs.
  • This approach provides a convenient method for fine-tuning the excited-state oxidation potential, essential for efficient charge transfer.
  • The synthesized dyes hold potential for enhancing the performance and stability of dye-sensitized solar cells.