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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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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...
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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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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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

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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...
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Naphthalimide Derivatives with Extended Heterocyclic Systems-Synthesis, Spectral and Sensing Properties.

Hristo Manov1, Ivo Grabchev2, Yulian Zagranyarski1

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Sensors (Basel, Switzerland)
|April 14, 2026
PubMed
Summary

This study designed novel naphthalimide derivatives as optical sensors. Benzofuran-annulated compounds effectively detected protons and metal ions via photoinduced electron transfer (PET), offering a new tool for chemical sensing.

Keywords:
1,8-naphthalimidesdensity functional theoryfluorescent sensorsheterocyclic annulationmetal ion sensingphotoinduced electron transfer

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Analytical Chemistry

Background:

  • 1,8-Naphthalimide derivatives are versatile fluorophores.
  • Photoinduced electron transfer (PET) is a key mechanism for optical sensing.
  • Designing selective and sensitive sensors requires careful control of electronic properties.

Purpose of the Study:

  • To design and evaluate π-extended 1,8-naphthalimide derivatives as PET optical sensors for protons and metal cations.
  • To investigate the impact of heterocyclic annulation and receptor-chromophore electronic matching on sensor performance.
  • To provide guidelines for the rational design of naphthalimide-based optical sensors.

Main Methods:

  • Synthesis of benzofuran- and benzodioxin-annulated naphthalimides with specific receptors.
  • Photophysical characterization using absorption and fluorescence spectroscopy.
  • Sensing performance evaluation via fluorescence titrations and quantum chemistry calculations.

Main Results:

  • Benzofuran-annulated naphthalimides showed strong fluorescence and efficient PET quenching upon receptor introduction.
  • Protonation and metal ion coordination (Cu(II), Sn(II)) suppressed PET, leading to significant fluorescence enhancement.
  • Benzodioxin-annulated derivatives exhibited poor sensing performance due to unfavorable electronic structures.

Conclusions:

  • Heterocyclic annulation is crucial for tuning the electronic structure and sensing capabilities of naphthalimide fluorophores.
  • Benzofuran annulation enables effective PET-based optical sensing of protons and metal ions.
  • The study offers rational design principles for developing advanced naphthalimide optical sensors.