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Related Concept Videos

Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry, similar...
Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...
Hybridization of Atomic Orbitals I03:24

Hybridization of Atomic Orbitals I

The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
Radical Chain-Growth Polymerization: Mechanism01:09

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The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this species into the...

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Published on: September 18, 2016

Fullerene/thiol-terminated molecules.

Yasuhiro Shirai1, Jason M Guerrero, Takashi Sasaki

  • 1Department of Chemistry, Smalley Institute for Nanoscale Science and Technology, Rice University, MS-222, 6100 Main Street, Houston, Texas 77005, USA.

The Journal of Organic Chemistry
|September 18, 2009
PubMed
Summary
This summary is machine-generated.

New fullerene-terminated oligo(phenylene ethynylene)s (OPEs) show potential for electronic devices. Their electronic properties, including narrow energy gaps, were confirmed by spectroscopy, revealing strong intermolecular interactions.

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Area of Science:

  • Materials Science
  • Organic Electronics
  • Nanotechnology

Background:

  • Oligo(phenylene ethynylene)s (OPEs) are conjugated molecules with tunable electronic properties.
  • Fullerenes are versatile carbon allotropes with unique electronic and photophysical characteristics.
  • Self-assembled monolayers (SAMs) are crucial for fabricating ordered thin films in electronic devices.

Purpose of the Study:

  • Synthesize and characterize fullerene-terminated OPEs for electronic and optoelectronic applications.
  • Investigate the electronic properties, including frontier orbital distribution and energy gaps.
  • Examine the behavior and electronic characteristics of these molecules in self-assembled monolayers on gold surfaces.

Main Methods:

  • Ab initio calculations (B3LYP/6-31G(d)) to determine electronic structures (HOMO/LUMO).
  • Ultraviolet photoelectron spectroscopy (UPS) to probe occupied electronic states.
  • Inverse photoelectron spectroscopy (IPES) to investigate unoccupied electronic states.

Main Results:

  • Calculations revealed frontier orbital localization on the fullerene cage.
  • A narrow distribution of Highest Occupied Molecular Orbital (HOMO)-Lowest Unoccupied Molecular Orbital (LUMO) energy gaps was observed.
  • Spectroscopic studies indicated strong intermolecular interactions in the SAMs and a small bandgap (~1.5 eV).

Conclusions:

  • Fullerene-terminated OPEs exhibit unique electronic properties due to orbital concentration on the fullerene.
  • The conjugated OPE backbone facilitates connection to the gold surface, influencing monolayer characteristics.
  • These materials hold promise for advanced electronic and optoelectronic device monolayers.