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Related Concept Videos

¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

2.4K
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...
2.4K
Spin–Spin Coupling: One-Bond Coupling01:17

Spin–Spin Coupling: One-Bond Coupling

1.2K
Coupling interactions are strongest between NMR-active nuclei bonded to each other, where spin information can be transmitted directly through the pair of bonding electrons. While nuclei polarize their electrons to the opposite spins, the bonding electron pair has opposite spins. Configurations with antiparallel nuclear spins are expected to be lower in energy. When coupling makes antiparallel states more favorable, J is considered to have a positive value. The one-bond coupling constant, 1J,...
1.2K
Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)01:20

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)

1.5K
Two NMR-active nuclei bonded to a central atom can be involved in geminal or two-bond coupling. Geminal coupling is commonly seen between diastereotopic protons in chiral molecules and unsymmetrical alkenes, among others.
The central atom need not be NMR-active because its electrons are affected by the electron polarization of the spin-active atoms. However, spin information is transmitted less effectively than in one-bond coupling, and 2J values are usually weaker than 1J values. The energy of...
1.5K
Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)01:22

Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)

1.3K
Vicinal or three-bond coupling is commonly observed between protons attached to adjacent carbons. Here, nuclear spin information is primarily transferred via electron spin interactions between adjacent C‑H bond orbitals. This generally favors the antiparallel arrangement of spins, so 3J values are usually positive.
The extent of coupling depends on the C‑C bond length, the two H‑C‑C angles, any electron-withdrawing substituents, and the dihedral angle between the...
1.3K
NMR Spectroscopy: Spin–Spin Coupling01:08

NMR Spectroscopy: Spin–Spin Coupling

3.3K
The spin state of an NMR-active nucleus can have a slight effect on its immediate electronic environment. This effect propagates through the intervening bonds and affects the electronic environments of NMR-active nuclei up to three bonds away; occasionally, even farther. This phenomenon is called spin–spin coupling or J-coupling. Coupling interactions are mutual and result in small changes in the absorption frequencies of both nuclei involved. While nuclei of the same element are involved...
3.3K
¹H NMR Signal Multiplicity: Splitting Patterns01:13

¹H NMR Signal Multiplicity: Splitting Patterns

6.9K
When protons A and X are coupled, their nuclear spin energy levels are slightly modified. This is because the energy required to excite proton A to a spin state parallel to proton X is slightly different from the energy required for it to become anti-parallel to spin X. Consequently, there are two possible excitation frequencies for A (A1 and A2), depending on the spin state of X, and vice versa. The mutual nature of coupling implies that the difference between frequencies A1 and A2, indicated...
6.9K

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Updated: Apr 22, 2026

Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry
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Strong Coupling in Orthogonal Nanographenes.

Luke T Lackovic1, Yann Lie2, Shayan Louie1

  • 1Department of Chemistry, Columbia University, New York City, New York, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 20, 2026
PubMed
Summary
This summary is machine-generated.

Researchers developed a new method to create contorted nanographenes, specifically a bay-fused dimer of dibenzoperylene (DBP[2]). This molecule exhibits unique electronic coupling and chiroptical properties, opening doors for advanced optoelectronics and energy storage applications.

Keywords:
chiralitycircularly polarized luminescenceelectronic couplinggraphene

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Nanotechnology

Background:

  • Octaphenyl cyclooctatetraene is a precursor molecule.
  • Graphene subunits and nanographenes are key materials in modern electronics.
  • Controlled electronic coupling is crucial for advanced material properties.

Purpose of the Study:

  • To report the cyclodehydrogenation of octaphenyl cyclooctatetraene.
  • To synthesize and characterize a novel bay-fused dimer of dibenzoperylene (DBP[2]).
  • To explore the electronic and chiroptical properties of the synthesized molecule.

Main Methods:

  • Cyclodehydrogenation reaction on molten alkali metal.
  • Spectroscopic measurements (e.g., UV-Vis absorption).
  • Electrochemical measurements.

Main Results:

  • Formation of DBP[2], a rigid, orthogonally fused nanographene structure.
  • Demonstration of strong electronic coupling and delocalization between nanographene moieties.
  • Observation of a pronounced chiroptical response in the chiral enantiomers of DBP[2].
  • DBP[2] acts as an efficient two-electron acceptor with broad visible light absorption.

Conclusions:

  • The novel cyclodehydrogenation reaction provides access to contorted nanographenes.
  • DBP[2] exhibits unique electronic and chiroptical properties due to its structure.
  • Contorted nanographenes have potential applications in optoelectronics, energy storage, and chiroptics.