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Structure of Benzene: Molecular Orbital Model

Structure of Benzene: Molecular Orbital Model

According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).

Radical Chain-Growth Polymerization: Overview

Radical Chain-Growth Polymerization: Overview

Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...

Nomenclature of Aromatic Compounds with Multiple Substituents

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When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

Structure of Benzene: Kekulé Model

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In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.

Reactions at the Benzylic Position: Halogenation

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.

Ziegler–Natta Chain-Growth Polymerization: Overview

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Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta...

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Extended Ladder-Type Benzo[k]tetraphene-Derived Oligomers.

Jongbok Lee¹, Huanbin Li², Alexander J Kalin¹

¹Department of Chemistry, Texas A&M University, 3255 TAMU, College Station, TX, 77843-3255, USA.

Angewandte Chemie (International Ed. in English)

|September 10, 2017

Summary

Researchers developed an efficient synthesis for extended benzo[k]tetraphene oligomers. This work clarifies structure-property relationships for advanced carbon materials, enabling optimized processing of highly ordered solids.

Keywords:

conjugation ladder polymers metathesis polycycles semiconductors

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Area of Science:

Organic Chemistry
Materials Science
Supramolecular Chemistry

Background:

Fused-ring aromatic oligomers are key for advanced carbon-rich materials.
Challenges exist in their bottom-up synthesis and structure-property correlation.

Purpose of the Study:

To develop an efficient synthetic route for extended benzo[k]tetraphene-derived oligomers.
To elucidate the molecular and electronic structures of these compounds.
To establish a precise correlation between molecular size, crystallization dynamics, and processing.

Main Methods:

Employed an efficient synthetic strategy to construct oligomers.
Utilized advanced techniques for molecular and electronic structure elucidation.
Investigated crystallization dynamics and their relationship with molecular size.

Main Results:

Successfully synthesized extended benzo[k]tetraphene-derived oligomers with up to 13 fused rings.
Clearly elucidated the molecular and electronic structures of the synthesized compounds.
Established a precise correlation between molecular size and crystallization dynamics.

Conclusions:

Demonstrated an efficient method for synthesizing complex fused-ring systems.
Highlighted the critical balance between intermolecular interactions and molecular mobility for processing.
Provided insights for optimizing the processing of highly ordered conjugated molecular solids.