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Crystal Field Theory - Octahedral Complexes02:58

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Crystal Field Theory
To explain the observed behavior of transition metal complexes (such as colors), a model involving electrostatic interactions between the electrons from the ligands and the electrons in the unhybridized d orbitals of the central metal atom has been developed. This electrostatic model is crystal field theory (CFT). It helps to understand, interpret, and predict the colors, magnetic behavior, and some structures of coordination compounds of transition metals.
CFT focuses on...
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Thermal Electrocyclic Reactions: Stereochemistry01:17

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Crystal Field Theory - Tetrahedral and Square Planar Complexes02:46

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Tetrahedral Complexes
Crystal field theory (CFT) is applicable to molecules in geometries other than octahedral. In octahedral complexes, the lobes of the dx2−y2 and dz2 orbitals point directly at the ligands. For tetrahedral complexes, the d orbitals remain in place, but with only four ligands located between the axes. None of the orbitals points directly at the tetrahedral ligands. However, the dx2−y2 and dz2 orbitals (along the Cartesian axes) overlap with the ligands less than the dxy,...
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Aromatic Hydrocarbon Cations: Structural Overview01:18

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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.
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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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Updated: May 25, 2025

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Manipulating Crystal Packing in Heterocycloarenes by an Atom Engineering Strategy for High-Mobility Organic

Rong Zhang1, Wenhao Li1, Yuanhe Gu1

  • 1Department of Materials Science, State Key Laboratory of Molecular Engineering of Polymers, Laboratory of Molecular Materials and Devices, Fudan University, Shanghai, 200438, China.

Angewandte Chemie (International Ed. in English)
|February 25, 2025
PubMed
Summary

Researchers synthesized novel ring-shaped organic semiconductors (OSCs) by engineering chalcogen atoms in heterocycloarenes. The sulfur-fused material achieved record hole mobility, demonstrating potential for advanced optoelectronics.

Keywords:
chalcogen atom engineeringcrystal packingheterocycloarenesring-shaped organic semiconductorssingle-crystal transistors

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Area of Science:

  • Materials Science
  • Organic Electronics
  • Supramolecular Chemistry

Background:

  • Developing high-performance organic semiconductors (OSCs) is crucial for optoelectronics.
  • Ring-shaped (hetero)cycloarenes offer potential but face synthetic challenges and limited material diversity.
  • Controlling molecular packing and intermolecular interactions is key to enhancing OSC performance.

Purpose of the Study:

  • To synthesize and investigate a series of coplanar chalcogen-fused heterocycloarenes (NO, NS, NSe).
  • To systematically elucidate the role of chalcogen atom engineering on the properties of these ring-shaped OSCs.
  • To explore their supramolecular interactions and potential for optoelectronic applications.

Main Methods:

  • Synthesis of novel heterocycloarenes (NO, NS, NSe) with long branched alkyl chains.
  • Single-crystal X-ray diffraction to analyze crystal packing and intermolecular interactions.
  • Measurement of charge carrier mobility to evaluate semiconductor performance.
  • Investigation of selective supramolecular interactions with C70.

Main Results:

  • The sulfur-fused NS derivative exhibited the closest herringbone crystal packing with a π-π stacking distance of 3.11 Å.
  • NS achieved a record-high hole mobility of 3.13 cm² V⁻¹ s⁻¹ among reported ring-shaped OSCs.
  • The selenium-fused NSe derivative, despite lacking intermolecular π-π interactions, showed the second-highest mobility (2.11 cm² V⁻¹ s⁻¹) due to edge-to-face Se…π and C-H…π interactions.
  • A selective trend in supramolecular binding constants with C70 was observed: NS < NO < NSe.

Conclusions:

  • Chalcogen atom engineering significantly impacts the crystal packing and charge transport properties of heterocycloarenes.
  • The study provides a systematic understanding of atom engineering effects on these emerging ring-shaped OSCs.
  • These findings pave the way for the practical application of novel heterocycloarenes in advanced optoelectronic devices.