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Alkyl Halides02:45

Alkyl Halides

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Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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Atoms and molecules interact through bonds (or forces): intramolecular and intermolecular. The forces are electrostatic as they arise from interactions (attractive or repulsive) between charged species (permanent, partial, or temporary charges) and exist with varying strengths between ions, polar, nonpolar, and neutral molecules. The different types of intermolecular forces are ion–dipole, dipole–dipole, hydrogen bonds, and dispersion; among these, dipole–dipole, hydrogen...
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Hydrogen Bonds01:04

Hydrogen Bonds

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A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
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Hydrogen Bonds00:26

Hydrogen Bonds

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Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

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Evidence for Interfacial Halogen Bonding.

Wesley B Swords1, Sarah J C Simon2, Fraser G L Parlane2

  • 1Department of Chemistry, The University of North Carolina at Chapel Hill, Murray Hall 2202B, Chapel Hill, NC, 27599-3290, USA.

Angewandte Chemie (International Ed. in English)
|April 11, 2016
PubMed
Summary
This summary is machine-generated.

Heavier halogen substituents on triphenylamine dyes accelerate dye regeneration kinetics. This effect is attributed to enhanced halogen bonding between the dye and iodide, crucial for dye-sensitized solar cells.

Keywords:
dyeshalogen bondinginorganic chemistryreaction kineticssemiconductor interfaces

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Area of Science:

  • Materials Science
  • Photochemistry
  • Organic Chemistry

Background:

  • Donor-π-acceptor dyes are crucial for light harvesting in solar cells.
  • Understanding substituent effects on dye performance is key to optimizing energy conversion.

Purpose of the Study:

  • To synthesize a homologous series of triphenylamine (TPA) dyes with varying halogen substituents (F, Cl, Br, I).
  • To investigate the impact of these halogen substituents on the dye regeneration kinetics after light-induced charge separation.

Main Methods:

  • Synthesis of a series of Dye-X (X=F, Cl, Br, I) molecules.
  • Immobilization of dyes onto a titanium dioxide (TiO2) surface.
  • Transient absorption spectroscopy to study the reaction kinetics with iodide.

Main Results:

  • Dye regeneration rates increased with halogen polarizability: Dye-F < Dye-Cl < Dye-Br < Dye-I.
  • The observed trend is linked to the electropositive σ-hole on heavier halogens.
  • Halogen bonding between the dye and nucleophilic iodide is proposed as the key interaction.

Conclusions:

  • Halogen substituents significantly influence dye regeneration kinetics in TiO2-based systems.
  • Heavier halogens enhance regeneration through stronger halogen bonding interactions.
  • This provides a pathway for designing more efficient dye-sensitized solar cells.