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Related Concept Videos

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...
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
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,...
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...
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...

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Related Experiment Video

Updated: Jun 4, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Macrocyclic hosts for fullerenes: extreme changes in binding abilities with small structural variations.

David Canevet1, María Gallego, Helena Isla

  • 1IMDEA-Nanociencia, Facultad de Ciencias, Ciudad Universitaria de Cantoblanco, E-28049 Madrid, Spain.

Journal of the American Chemical Society
|February 16, 2011
PubMed
Summary

Researchers developed new macrocyclic hosts with π-extended tetrathiafulvalene (exTTF) units. These hosts exhibit world-record binding affinities for C(60) fullerenes, showcasing tailored molecular recognition.

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Preparation and Characterization of C60/Graphene Hybrid Nanostructures
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Preparation and Characterization of C60/Graphene Hybrid Nanostructures

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Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry

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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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Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry
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Published on: March 4, 2021

Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Fullerenes (C(60) and C(70)) possess unique electronic and structural properties.
  • Developing selective and high-affinity host molecules for fullerenes is a significant challenge in molecular recognition.
  • π-extended tetrathiafulvalene (exTTF) derivatives offer promising electronic and shape complementarity for fullerene binding.

Purpose of the Study:

  • To fine-tune macrocyclic bis-exTTF hosts for enhanced binding of C(60) and C(70) fullerenes.
  • To investigate the impact of structural variations in aromatic spacers and linker lengths on fullerene complexation.
  • To explore the structure-affinity relationships in a new family of all-organic fullerene receptors.

Main Methods:

  • Synthesis of nine novel macrocyclic bis-exTTF receptors with varied aromatic spacers (p-xylene, m-xylene, 2,6-dimethylnaphthalene) and linker lengths.
  • Utilizing ring-closing metathesis for macrocycle formation.
  • UV-vis titrations to quantitatively assess binding affinities and stoichiometries with C(60) and C(70).
  • Preliminary molecular modeling to guide structural design.

Main Results:

  • Achieved high binding constants for C(60) complexation, with log K(a) up to 6.5 ± 0.5 in chlorobenzene, representing a record for all-organic receptors.
  • Demonstrated that minor structural modifications in the macrocyclic hosts significantly alter binding affinity and, in some cases, complex stoichiometry.
  • Identified specific structural features that enhance recognition of C(60) and C(70) fullerenes.

Conclusions:

  • The study presents a new family of highly effective all-organic macrocyclic hosts for fullerenes.
  • The results underscore the importance of precise structural control in host-guest chemistry, particularly for challenging guests like fullerenes.
  • The electronic and geometrical complementarity between exTTF units and fullerenes is key to the observed strong and stable complex formation.