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Related Concept Videos

Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

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Antifouling Self-assembled Monolayers on Microelectrodes for Patterning Biomolecules
10:27

Antifouling Self-assembled Monolayers on Microelectrodes for Patterning Biomolecules

Published on: August 25, 2009

Monolayer patterning using ketone dipoles.

Min Kyoung Kim1, Yi Xue, Tereza Pašková

  • 1Department of Chemistry, Brown University, Providence, RI, USA.

Physical Chemistry Chemical Physics : PCCP
|May 2, 2013
PubMed
Summary
This summary is machine-generated.

Ketone groups enable patterned self-assembled monolayers by creating dipolar attraction. These molecules spontaneously form compositionally patterned monolayers driven by side chain interactions, comparable to CF2 groups.

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Area of Science:

  • Surface Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Self-assembly of multi-component monolayers requires molecular recognition.
  • Dipolar interactions influence self-assembled monolayer morphology and molecular recognition.
  • Ketone groups possess large dipole moments and are easily incorporated into molecules.

Purpose of the Study:

  • To evaluate the potential of ketone groups for dipolar patterning in self-assembled monolayers.
  • To synthesize and characterize anthracene derivatives with mono-ketone side chains.
  • To investigate the energetics and morphology of self-assembled monolayers formed by these compounds.

Main Methods:

  • Synthesis of two 1,5-disubstituted anthracenes with mono-ketone side chains.
  • Scanning Tunneling Microscopy (STM) characterization of self-assembled monolayers.
  • Molecular mechanics simulations to determine self-assembly energetics.

Main Results:

  • Anthracenes with self-repulsive mono-ketone side chains form monolayers with atypical morphology, establishing dipolar attraction between adjacent side chains.
  • Dipolar complementary anthracene pairs spontaneously assemble into compositionally patterned monolayers with segregated single-component columns.
  • Patterned monolayers form from complementary pairs using different dipolar groups (ketones or CF2 groups).
  • Ketone groups provide a driving force for patterned monolayer formation comparable to CF2 groups, despite differences in dipole moment and size.

Conclusions:

  • Ketone groups are effective for creating dipolar attraction and enabling patterned self-assembly in monolayers.
  • Spontaneous formation of compositionally patterned monolayers is achievable through specific side chain dipolar interactions.
  • The size and dipole moment of the functional group influence the driving force for patterned monolayer formation.