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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.
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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.

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Related Experiment Video

Updated: Jun 5, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

Synthesis and Acid-Sensing Behavior of Rhodamine-Thiazolothiazole Conjugates.

João M O Silva1, Fábio Martins1, Juliana Machado1,2

  • 1LAQV-REQUIMTE, Department of Chemistry and Biochemistry (DQB), Faculty of Sciences, University of Porto (FCUP), Porto, Portugal.

Chempluschem
|June 4, 2026
PubMed
Summary

Novel fluorescent probes, RhodTzTzCHO and RhodTzTzRhod, show unique pH-dependent behavior. These rhodamine-thiazolo[5,4-d]thiazole conjugates selectively detect trifluoroacetic acid, offering potential for specific acid sensing applications.

Keywords:
acid‐sensing behaviorprotonationrhodamine hydrazidespirocyclic ring openingthiazolothiazole

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Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

Published on: March 6, 2019

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Analytical Chemistry

Background:

  • Rhodamine derivatives are known fluorescent probes but often susceptible to pH changes.
  • Thiazolo[5,4-d]thiazole (TzTz) cores offer unique electronic properties.
  • Developing selective fluorescent sensors for specific acidic environments remains a challenge.

Purpose of the Study:

  • To synthesize and characterize novel fluorescent conjugates integrating rhodamine B hydrazide with a TzTz core.
  • To investigate the unusual pH-dependent behavior and acid-sensing capabilities of these conjugates.
  • To explore the factors influencing the stability and ring-opening mechanism of the conjugates in acidic media.

Main Methods:

  • Synthesis of RhodTzTzCHO and RhodTzTzRhod conjugates.
  • Spectroscopic characterization (UV-Vis, fluorescence).
  • Nuclear Magnetic Resonance (NMR) and Mass Spectrometry (MS) for structural elucidation.
  • Density Functional Theory (DFT) calculations to study protonation and electronic properties.

Main Results:

  • The novel RhodTzTzCHO and RhodTzTzRhod conjugates were successfully synthesized and characterized.
  • These conjugates remained nonfluorescent in various acids (HCl, H2SO4, acetic acid) but fluoresced intensely in trifluoroacetic acid (TFA).
  • DFT calculations and spectroscopic data revealed that electronic properties and solvent effects stabilize the closed spirolactam form, even under protonation, especially in dimethylformamide (DMF).

Conclusions:

  • The rhodamine-TzTz conjugates exhibit exceptional stability in most acidic conditions, with selective ring-opening and fluorescence activation exclusively by TFA.
  • This selectivity is attributed to the electronic interplay between the rhodamine, TzTz core, and phenyl bridges, along with solvent effects.
  • These findings highlight the potential of these conjugates as robust and selective fluorescent sensors for specific acidic analytes in complex environments.