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Related Concept Videos

¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR01:15

¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR

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The axial and equatorial protons in cyclohexane can be distinguished by performing a variable-temperature NMR experiment. In this process, except for one proton, the remaining eleven protons are replaced by deuterium. The deuterium substitution avoids the possible peak splitting caused by the spin-spin coupling between the adjacent protons. The remaining proton flips between the axial and equatorial positions.
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Polymer Classification: Stereospecificity01:26

Polymer Classification: Stereospecificity

2.4K
Polymerization generates chiral centers along the entire backbone of a polymer chain. Accordingly, the stereochemistry of the substituent group has a significant effect on polymer properties. Polymers formed from monosubstituted alkene monomers feature chiral carbons at every alternate position in the polymer backbone. Relative to the predominant orientation of substituents at the adjacent chiral carbons, the polymer can exist in three different configurations: isotactic, syndiotactic, and...
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Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

12.0K
Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
12.0K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

12.6K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
12.6K
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

847
At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
847
Thermal Sigmatropic Reactions: Overview01:16

Thermal Sigmatropic Reactions: Overview

2.1K
Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in...
2.1K

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Mesomorphism Modulation of Perfluorinated Janus Triphenylenes by Inhomogeneous Chain Substitution Patterns.

Kai-Li Zhang1, Wen-Hao Yu1, Ke-Qing Zhao1

  • 1College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, 610066, China.

Chemistry, an Asian Journal
|January 12, 2024
PubMed
Summary

New fluorinated triphenylenes exhibit unique columnar mesophases and blue-violet fluorescence. Their properties depend on chain length and isomerism, offering potential for advanced materials.

Keywords:
Triphenylenearene-perfluoroarene interactionsconstitutional isomerismcrystal structurediscotic liquid crystalfluorescencenucleophilic substitution reaction of fluoroarene SNAr

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Triphenylene derivatives are known for their liquid crystalline and photophysical properties.
  • Fluorination can significantly alter molecular packing and electronic characteristics.
  • Understanding structure-property relationships is crucial for designing new functional materials.

Purpose of the Study:

  • To synthesize and characterize novel fluorinated and non-fluorinated triphenylene isomers.
  • To investigate the impact of chain length and positional isomerism on mesophase behavior.
  • To explore the photophysical properties, including fluorescence, of these compounds.

Main Methods:

  • Synthesis via efficient, transition-metal-free fluoroarene nucleophilic substitution.
  • Characterization using single-crystal X-ray diffraction to confirm structures.
  • Differential scanning calorimetry and polarized optical microscopy to study mesomorphism.

Main Results:

  • Successful synthesis of two isomeric series of fluorinated (p-TPFn, m-TPFn) and non-fluorinated (p-TP4, m-TP4) triphenylenes.
  • Fluorinated compounds form columnar hexagonal (Colhex) mesophases, influenced by chain length and isomerism.
  • Blue-violet fluorescence observed in solution (up to 46% quantum yield), slightly redshifted in thin films.

Conclusions:

  • Positional isomerism and alkyl chain length critically control the mesomorphism of fluorinated triphenylenes.
  • Fluorinated triphenylenes exhibit distinct columnar phases, while non-fluorinated analogs lack mesomorphism.
  • These compounds show promising photophysical properties for potential optoelectronic applications.