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Related Concept Videos

Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

4.5K
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,...
4.5K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.2K
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...
3.2K
¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

2.0K
The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
2.0K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.1K
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...
3.1K
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

10.4K
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
10.4K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

3.1K
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
3.1K

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Updated: Oct 10, 2025

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Parallel-stacked aromatic molecules in hydrogen-bonded inorganic frameworks.

Masayasu Igarashi1, Takeshi Nozawa2, Tomohiro Matsumoto2

  • 1Interdisciplinary Research Center for Catalytic Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, 305-8565, Japan. masayasu-igarashi@aist.go.jp.

Nature Communications
|December 11, 2021
PubMed
Summary

Researchers developed hydrogen-bonded inorganic frameworks (HIFs) using silica building blocks. These HIFs enable the infinite parallel π-stacking of various organic molecules, creating novel functional materials.

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Formation of Ordered Biomolecular Structures by the Self-assembly of Short Peptides
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Area of Science:

  • Materials Science
  • Supramolecular Chemistry
  • Inorganic Chemistry

Background:

  • Precise molecular construction and supramolecular assembly yield novel properties and functionalities.
  • Understanding reversible weak interactions like hydrogen bonds and π-π interactions is key for developing advanced materials.
  • Hydrogen-bonded organic frameworks (HOFs) offer a strategy for designing functional materials.

Purpose of the Study:

  • To adapt the HOFs strategy for inorganic materials science.
  • To utilize the cubic octamer of orthosilicic acid, [Si8O12][OH]8, as a building block for inorganic frameworks.
  • To explore the creation of hydrogen-bonded inorganic frameworks (HIFs) and their properties.

Main Methods:

  • Employed the hydrogen-bonded organic frameworks (HOFs) strategy with inorganic building blocks.
  • Used the cubic octamer of orthosilicic acid, [Si8O12][OH]8, as a precursor.
  • Investigated the assembly of organic molecules within the pores of the synthesized HIFs.

Main Results:

  • Successfully synthesized various types of hydrogen-bonded inorganic frameworks (HIFs).
  • Achieved infinite parallel π-stacking of pure benzene, thiophene, selenophene, p-benzoquinone, and their co-polymers within the HIFs.
  • Demonstrated that these polymers interact via their π-systems within the flexible pores of the 3D nano-honeycomb HIFs.

Conclusions:

  • The HOFs strategy can be successfully applied to inorganic materials science.
  • The developed HIFs provide a platform for creating ordered π-stacked polymer structures.
  • This approach opens new avenues for designing materials with tailored functionalities based on π-system interactions.