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Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

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The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
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Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
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Different notations are used to represent the three-dimensional structure of molecules on two-dimensional surfaces. One of the most commonly used representations is the dash-wedge formula. The dashed wedges, solid wedges, and the plane lines indicate the groups situated behind the plane, coming out of the plane, and in the plane, respectively.
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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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Life on Earth is carbon-based, as all macromolecules that make up living organisms contain carbon atoms. All organic compounds have a carbon backbone. Each carbon atom is tetravalent and can bond with four other atoms, making it an extraordinarily flexible component of biological molecules. Because carbon’s valence electrons are stable, it rarely becomes an ion. As the carbon chain increases in length, structural modifications such as ring structures, double bonds, and branching side...
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Microfluidic-based Synthesis of Covalent Organic Frameworks COFs: A Tool for Continuous Production of COF Fibers and Direct Printing on a Surface
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Soft Hydrogen-Bonded Organic Frameworks Constructed Using a Flexible Organic Cage Hinge.

Qiang Zhu1,2, Lei Wei3, Chengxi Zhao1,4

  • 1Department of Chemistry and Materials Innovation Factory, University of Liverpool, Liverpool L7 3NY, U.K.

Journal of the American Chemical Society
|October 12, 2023
PubMed
Summary

Researchers developed a flexible organic cage molecule, Cage-6-COOH, forming hydrogen-bonded organic frameworks (HOFs). This molecule exhibits unique structural transformations and self-healing properties, creating porous materials with potential applications.

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Layer-by-layer Synthesis and Transfer of Freestanding Conjugated Microporous Polymer Nanomembranes
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Area of Science:

  • Materials Science
  • Supramolecular Chemistry
  • Crystallography

Background:

  • Soft porous crystals offer tunable responses to stimuli but achieving both flexibility and porosity in molecular crystals is difficult.
  • Weak intermolecular interactions in molecular crystals often limit structural stability and porosity.

Purpose of the Study:

  • To design and synthesize a flexible organic cage molecule with hinge-like motion for constructing hydrogen-bonded organic frameworks (HOFs).
  • To investigate the structural diversity and properties of HOFs derived from the flexible cage, focusing on porosity and responsiveness.
  • To explore the self-healing and structural memory capabilities of these novel HOFs.

Main Methods:

  • Synthesis of a flexible oxygen-bridged prismatic organic cage molecule (Cage-6-COOH).
  • Formation of hydrogen-bonded organic frameworks (HOFs) using Cage-6-COOH under varying conditions.
  • Structural characterization of the resulting HOFs, including two interpenetrated structures (CageHOF-2α and CageHOF-2β), using techniques like X-ray diffraction.
  • Assessment of porosity and surface area (e.g., BET analysis for CageHOF-2β).

Main Results:

  • A flexible organic cage, Cage-6-COOH, with a 67° dihedral angle range due to its hinge-like motion was successfully synthesized.
  • Two novel interpenetrated HOFs, CageHOF-2α (nonporous) and CageHOF-2β (porous, 458 m²/g surface area), were formed.
  • Cage-6-COOH readily transformed into these HOFs via solvent vapor treatment, demonstrating rapid self-healing and selective structural memory in CageHOF-2β.

Conclusions:

  • The flexible Cage-6-COOH molecule enables the construction of structurally diverse HOFs with tunable porosity.
  • The inherent molecular flexibility and noncovalent interactions facilitate significant structural transformations and self-healing.
  • These findings highlight the potential of flexible organic cages for designing adaptive and responsive porous materials.