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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.8K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
3.4K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

6.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

2.3K
Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
2.3K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

5.2K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
5.2K
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

12.0K
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
12.0K

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Supramolecular nesting of cyclic polymers.

Dmitry V Kondratuk, Luís M A Perdigão, Ayad M S Esmail

    Nature Chemistry
    |May 15, 2015
    PubMed
    Summary

    Researchers synthesized large cyclic porphyrin polymers up to 21 nm wide. These synthetic macromolecules exhibit unique self-organization behaviors, forming nested and stacked structures on surfaces.

    Area of Science:

    • Supramolecular Chemistry
    • Polymer Science
    • Nanotechnology

    Background:

    • Template-directed synthesis enables creation of artificial macromolecules with protein-like dimensions.
    • Synthetic macromolecules can exhibit self-organization properties similar to biopolymers.

    Purpose of the Study:

    • To synthesize monodisperse cyclic porphyrin polymers with large diameters.
    • To investigate the solution behavior and self-organization of these cyclic polymers on surfaces.

    Main Methods:

    • Synthesis of monodisperse cyclic porphyrin polymers.
    • Viscosity measurements to determine solution behavior.
    • Scanning tunneling microscopy (STM) for surface analysis.

    Main Results:

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    • Successfully synthesized cyclic porphyrin polymers up to 21 nm in diameter (750 C–C bonds).
    • Solution behavior approximates ideal flexible chains (intrinsic viscosity ratio of 0.72).
    • Observed novel 2D supramolecular organization on gold surfaces, including encapsulation and nesting.
    • STM revealed vacuum deposition leads to combined nesting and stacking, while solution deposition results in either nesting or stacking.

    Conclusions:

    • Large cyclic porphyrin polymers can be synthesized with controlled dimensions.
    • These polymers exhibit unique self-assembly behaviors, forming complex nanostructures.
    • The method of deposition influences the resulting supramolecular organization.