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Related Concept Videos

ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

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...
[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.
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

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 on...
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.
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...

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Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
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Highly intense fluorescent diarylboron diketonate.

Atsushi Nagai1, Kenta Kokado, Yuuya Nagata

  • 1Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.

The Journal of Organic Chemistry
|October 11, 2008
PubMed
Summary

New diarylboron diketonate compounds were synthesized. Their fluorescence intensity varied with arylboron substituents, with a C6F5 group yielding the brightest emission.

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Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores

Published on: August 19, 2013

Area of Science:

  • Organometallic Chemistry
  • Materials Science
  • Photophysics

Background:

  • 1,3-diketone derivatives are versatile ligands in coordination chemistry.
  • Arylboron compounds offer tunable electronic properties for materials applications.
  • Fluorescent organic materials are crucial for sensing and optoelectronic devices.

Purpose of the Study:

  • To synthesize novel diarylboron diketonate complexes.
  • To investigate the influence of arylboron substituents on the photophysical properties of these complexes.
  • To identify structural features that enhance fluorescent emission.

Main Methods:

  • Reaction of 1,3-diketone derivatives with arylboron compounds (e.g., triphenylborane, fluorobis(pentafluorophenyl)borane diethyl etherate).
  • Characterization of the synthesized diarylboron diketonates.
  • Spectroscopic analysis to determine fluorescent emission properties.

Main Results:

  • Successful synthesis of diarylboron diketonate complexes.
  • Fluorescent emission was observed and found to be dependent on the arylboron moiety's substituents.
  • The complex featuring a 1,3-bis(4-methoxyphenyl)-1,3-diketonate ligand chelated by a pentafluorophenyl (C6F5) group exhibited the most intense fluorescence.

Conclusions:

  • Diarylboron diketonates can be effectively prepared using arylboron compounds.
  • The electronic nature of the arylboron substituent significantly impacts the fluorescence of the resulting complexes.
  • Strong electron-withdrawing groups, such as C6F5, can enhance the fluorescence intensity of diarylboron diketonates.