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Related Concept Videos

Cohesion01:07

Cohesion

Cohesion is the attraction between molecules of the same type, such as water molecules. Water molecules have an overall neutral charge but are polar molecule. An oxygen atom in one water molecule has a partial negative charge that can bind to a hydrogen atom with a partial positive charge in a second water molecule, forming a hydrogen bond. Each water molecule can form up to four hydrogen bonds with other water molecules. Hydrogen bonds are responsible for water's cohesive nature.
On a surface,...
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Dehydration Synthesis

Dehydration synthesis (also called a condensation reaction) is the chemical process in which two molecules covalently link together to form a new molecule, along with the release of a water molecule. Many physiologically important compounds form by dehydration synthesis reactions, such as complex carbohydrates, proteins, DNA, and RNA.Synthesis of carbohydratesSugar molecules are covalently linked together by dehydration synthesis. During the reaction, the hydroxyl (-OH) group from one reactant...
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Solution Formation

There is no one solvent that can dissolve every type of solute. Some substances that readily dissolve in a certain solvent might be insoluble in a different solvent. A simple way to predict which substances dissolve in which solvent is the phrase "like dissolves like". This means that polar substances, such as salt and sugar, dissolve in a polar substance like water. In contrast, non-polar substances are more soluble in non-polar solvents such as carbon tetrachloride.
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Intermolecular Forces in Solutions02:28

Intermolecular Forces in Solutions

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Colloids

Children at play often make suspensions such as mixtures of mud and water, flour and water, or a suspension of solid pigments in water known as tempera paint. These suspensions are heterogeneous mixtures composed of relatively large particles that are visible to the naked eye or can be seen with a magnifying glass. They are cloudy, and the suspended particles settle out after mixing. On the other hand, a solution is a homogeneous mixture in which no settling occurs and in which the dissolved...
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Solution, Solubility, and Solubility Equilibrium
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Synthesis of a Water-soluble Metal&#8211;Organic Complex Array
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Aromatic oligomers that form hetero duplexes in aqueous solution.

Gregory J Gabriel1, Brent L Iverson

  • 1Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas, USA.

Journal of the American Chemical Society
|December 19, 2002
PubMed
Summary

Researchers created stable molecular duplexes in water using complementary aromatic units. This novel self-assembly method, driven by pi-pi interactions between electron-deficient Naphthalenetetracarboxylic diimide (Ndi) and electron-rich Dialkoxynaphthalene (Dan) units, offers programmable binding.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Electron-deficient 1,4,5,8-naphthalenetetracarboxylic diimide (Ndi) and electron-rich 1,5-dialkoxynaphthalene (Dan) exhibit strong complexation in water via hydrophobic effects and electrostatic complementarity.
  • Previous work demonstrated foldamers (aedamers) using intramolecular aromatic stacking for secondary structure formation in nonnatural chains.
  • Aromatic stacking, or pi-pi interactions, are key to molecular recognition and self-assembly.

Purpose of the Study:

  • To demonstrate the intermolecular self-assembly of stable hetero duplexes using complementary Ndi and Dan units in aqueous solution.
  • To investigate the binding stoichiometry, thermodynamics, and stability of these self-assembled duplexes.
  • To establish a new system for designing programmable molecular assemblies.

Main Methods:

  • Synthesis of molecular strands incorporating Ndi (1a-4a) and Dan (1b-4b) units.
  • Nuclear Magnetic Resonance (NMR) spectroscopy and Isothermal Titration Calorimetry (ITC) to determine binding stoichiometry and thermodynamics.
  • Polyacrylamide Gel Electrophoresis (PAGE) to assess interaction strength and binding modes.

Main Results:

  • Stable hetero duplexes were successfully formed through intermolecular aromatic (pi-pi) interactions between Ndi and Dan strands.
  • NMR and ITC confirmed a 1:1 binding stoichiometry, with association being enthalpically favored.
  • The tetra-Ndi (4a) and tetra-Dan (4b) strands formed a hetero duplex (4a:4b) with a high stability constant (350,000 M⁻¹ at 318 K).
  • PAGE results supported the strong interaction and 1:1 binding mode.

Conclusions:

  • This study presents the first system to utilize complementary aromatic units for discrete self-assembly in aqueous solution via intermolecular pi-pi interactions.
  • The developed system demonstrates highly programmable binding capabilities, paving the way for future duplex systems.
  • This approach holds promise for designing novel molecular assemblies in solution and on surfaces.