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Related Concept Videos

Conformations of Cyclohexane02:11

Conformations of Cyclohexane

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.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal tetrahedral value,...
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

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.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...
Newman Projections02:06

Newman Projections

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.
The organic molecules rotate across the single bonds leading to numerous temporary three-dimensional structures of varying energy known as conformers.
Prochirality02:05

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that was based on the...
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...

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Related Experiment Video

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

Columnar structures from asymmetrically tapered biphenylamide.

Soo-Jin Park1, Seok-Ho Hwang, Namil Kim

  • 1Polymer Materials Fusion Research Center and Department of Polymer-Nano Science and Technology, Chonbuk National University, Jeonju 561-756, Korea.

The Journal of Physical Chemistry. B
|September 22, 2009
PubMed
Summary

A new cone-shaped molecule, asym-C(12)PhA, self-assembles into ordered columnar structures. These structures transition from a mesophase to a crystalline phase upon cooling, forming braided fibers.

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Area of Science:

  • Materials Science
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Design and synthesis of novel molecules with specific self-assembly properties are crucial for developing advanced materials.
  • Understanding the relationship between molecular structure and supramolecular organization is key to controlling material properties.
  • Asymmetrically tapered molecules offer unique possibilities for creating complex self-assembled architectures.

Purpose of the Study:

  • To design and synthesize a novel asymmetrically tapered biphenylamide molecule, denoted asym-C(12)PhA.
  • To investigate the self-assembly behavior and phase transitions of the synthesized asym-C(12)PhA.
  • To elucidate the supramolecular structures formed by asym-C(12)PhA at different temperatures.

Main Methods:

  • Synthesis of asymmetrically tapered N,N'-tris[[(2-dodecylaminocarbonyl)ethyl]methyl]-4-biphenylamide (asym-C(12)PhA).
  • Characterization of phase transitions and supramolecular structures using differential scanning calorimetry, 1D wide-angle X-ray diffraction (1D WAXD), Fourier-transform infrared spectroscopy, and solid-state (13)C nuclear magnetic resonance.
  • Analysis of self-assembled morphology using transmission electron microscopy (TEM) with selected area electron diffraction and cross-polarized optical microscopy.

Main Results:

  • The asym-C(12)PhA molecule exhibits a cone-like 3D geometry (3.01 nm height, 1.44 nm bottom radius).
  • Asym-C(12)PhA self-assembles into a highly ordered columnar mesophase below the isotropization temperature.
  • Upon further cooling, the mesophase transforms into a 3D columnar crystalline phase (Phi(Cr)), characterized by stacked discotic building blocks forming columns, which then laterally intercalate.
  • Self-assembled fibers of asym-C(12)PhA, approximately 1 µm in diameter and several millimeters in length, were observed to be braids of tiny single crystals.

Conclusions:

  • The designed asymmetrically tapered biphenylamide molecule, asym-C(12)PhA, successfully self-assembles into ordered supramolecular structures.
  • The study demonstrates a clear transition from a columnar mesophase to a 3D columnar crystalline phase driven by temperature changes.
  • The findings highlight the potential of asymmetrically tapered molecules in creating complex, ordered fibrous materials.