A Modular and Size‐Selective Synthesis of [n]Cycloparaphenylenes: A Step toward the Selective Synthesis of [n,n] Single‐Walled Carbon Nanotubes

Haruka Omachi; Sanae Matsuura; Yasutomo Segawa; Kenichiro Itami

doi:10.1002/ange.201005734

November 23, 2010Angewandte Chemie

A Modular and Size‐Selective Synthesis of [n]Cycloparaphenylenes: A Step toward the Selective Synthesis of [n,n] Single‐Walled Carbon Nanotubes

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Key Points

Establish a modular, size-controlled synthetic route to access large [n]cycloparaphenylenes as structural templates for uniform single-walled carbon nanotubes.
Coupled L-shaped cis-1,4-diphenylcyclohexane units with linear benzene or biphenyl building blocks via Suzuki-Miyaura reactions in [3+1+3] and [3+2+3] modes.
Assembled U-shaped septiphenyl and octiphenyl intermediate motifs.
Subjected U-shaped precursors to cyclizing dimerization followed by aromatization.
Achieved the size-selective synthesis of [14]-, [15]-, and [16]cycloparaphenylene macrocycles.
Established a versatile coupling strategy that directs ring diameter through the precise choice of linear bridging units.

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Implication

Synthetic study demonstrates modular assembly of [14]-, [15]-, and [16]cycloparaphenylenes in molecular precursors, highlighting progress toward uniform carbon nanotubes.

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Omachi et al. (2010) studied this question.

synapsesocial.com/papers/6a8ad18a2448cb7c68337187 https://doi.org/10.1002/ange.201005734

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A Modular and Size‐Selective Synthesis of [n]Cycloparaphenylenes: A Step toward the Selective Synthesis of [n,n] Single‐Walled Carbon Nanotubes

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No abstract yet

Implication

Discussion

Cite This Study

A Modular and Size‐Selective Synthesis of [n]Cycloparaphenylenes: A Step toward the Selective Synthesis of [n,n] Single‐Walled Carbon Nanotubes

Key Points

No abstract yet

Implication

Discussion

Cite This Study

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