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Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

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Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Modified-Release Drug Delivery Systems: Stimuli-Activated01:30

Modified-Release Drug Delivery Systems: Stimuli-Activated

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Stimuli-activated drug delivery systems are designed to release drugs in response to specific physical, chemical, or biological stimuli. These systems often utilize hydrogels—three-dimensional, hydrophilic polymer networks capable of swelling in aqueous environments and retaining significant fluid volumes. Upon exposure to particular stimuli, these hydrogels undergo structural transitions that allow the embedded drug to be released. Due to this adaptive behavior, such systems are also...
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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 para...
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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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.
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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Dipyrrolylpyrimidines as anion-responsive π-electronic systems.

Yohei Haketa1, Yuki Tamura, Nobuhiro Yasuda

  • 1Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, Kusatsu 525-8577, Japan. maedahir@ph.ritsumei.ac.jp.

Organic & Biomolecular Chemistry
|August 11, 2016
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Summary

Dipyrrolylpyrimidines show anion-binding capabilities due to pyrrole ring inversion. These molecules form unique columnar structures with anions and cations in the solid state, revealing novel supramolecular arrangements.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Dipyrrolylpyrimidines are heterocyclic compounds with potential applications in molecular recognition.
  • Anion binding is a crucial process in chemical sensing and biological systems.
  • Understanding the solid-state behavior of molecular complexes is essential for materials design.

Purpose of the Study:

  • To investigate the anion-binding properties of newly synthesized dipyrrolylpyrimidines.
  • To explore the solid-state structural characteristics of dipyrrolylpyrimidine-anion complexes.
  • To elucidate the role of pyrrole ring inversion in anion recognition.

Main Methods:

  • Synthesis of dipyrrolylpyrimidines via coupling reactions.
  • Anion binding studies using various anions.
  • Single-crystal X-ray diffraction analysis of anion complexes.
  • Solid-state structural characterization.

Main Results:

  • Synthesized dipyrrolylpyrimidines demonstrated significant anion-binding abilities.
  • Pyrrole ring inversion was observed upon anion complexation.
  • Complexes adopted charge-by-charge columnar structures in the solid state.
  • These structures involved the ordered assembly of dipyrrolylpyrimidine-anion units with counter cations.

Conclusions:

  • Dipyrrolylpyrimidines are effective anion receptors, with pyrrole ring inversion being a key feature.
  • The formation of columnar supramolecular structures highlights their potential in creating ordered materials.
  • This study provides insights into the rational design of anion-binding molecules and functional solid-state assemblies.