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2022•European Journal of Organic ChemistryOpen access

Manifestations of Antiaromaticity in Organic Materials: Case Studies of Cyclobutadiene, Borole, and Pentalene

Calvin Hong, J. C. Baltazar, John D. Tovar

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Abstract

Abstract This Review surveys the experimental and synthetic history of three classic antiaromatic cores: cyclobutadiene, borole, and pentalene. The coverage extends from the bare molecular cores to fused or substituted variants that impart thermodynamic or kinetic stability to the antiaromatic systems. Recent studies to utilize the unusual properties of these antiaromatic cores in the context of advanced electronic materials are discussed.

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Abstract This Review surveys the experimental and synthetic history of three classic antiaromatic cores: cyclobutadiene, borole, and pentalene. The coverage extends from the bare molecular cores to fused or substituted variants that impart thermodynamic or kinetic stability to the antiaromatic systems. Recent studies to utilize the unusual properties of these antiaromatic cores in the context of advanced electronic materials are discussed.

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Available abstract

Abstract This Review surveys the experimental and synthetic history of three classic antiaromatic cores: cyclobutadiene, borole, and pentalene. The coverage extends from the bare molecular cores to fused or substituted variants that impart thermodynamic or kinetic stability to the antiaromatic systems. Recent studies to utilize the unusual properties of these antiaromatic cores in the context of advanced electronic materials are discussed.

Key concepts: Antiaromaticity, Cyclobutadiene, Pentalene, Context (archaeology), Chemistry, Computational chemistry, Organic chemistry, Geology

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