苯在200度
Benzene at 200

原始链接: https://www.chemistryworld.com/opinion/benzene-at-200/4021504.article

1825年,迈克尔·法拉第分离出苯,这种化合物彻底改变了化学。它独特的芳香气味和令人惊讶的稳定性,难以用当时的理论进行归类,最终促进了人们对其环状结构的理解和芳香化学的发展。苯溶解非极性物质的能力使其成为宝贵的溶剂,而其反应性和稳定性则催生了整个有机化学分支。 苯的遗产延伸到多环芳烃(PAHs),例如六苯并稠苯、纳米石墨烯,最终到石墨烯。石墨烯是由稠合苯环组成的单层片状材料,具有非凡的特性,有望彻底改变电子学、储能和医学领域。 苯也是化学教育的基石,用于教授芳香性、共振等基本概念。为了庆祝苯发现200周年,英国皇家化学学会将出版特刊,重点介绍其对碳基体系的深远影响,从芳香性到石墨烯、碳纳米管和富勒烯的突破性研究,巩固了苯对科学的持久影响,并激励着未来几代化学家。

Hacker News上关于“苯的200周年”一文的讨论总结如下: 文章庆祝苯发现200周年,强调了其在化学中的重要性及其独特结构背后的神秘之处。讨论引发了多种不同的反应。一些人分享了与苯接触及其健康影响相关的个人轶事,而另一些人则指出文章忽略了凯库勒关于苯环结构的著名梦境。 讨论深入探讨了苯的历史应用背景,一些人回忆起它过去作为溶剂的应用及其与白血病等健康风险的关联。评论者还讨论了其现代用途(作为溶剂)以及其在生产其他化学品中的作用。有用户分享了展示苯分子结构的Instagram帖子链接。讨论还涉及到致癌物分类的复杂性以及关于不同情况下苯接触的相对危险性的持续争论。一位用户批评强生公司被指控其婴儿爽身粉中含有苯,而实际情况与石棉有关,并同意在未来的声明中更加准确。
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原文

Benzene and bunting in chalk on a blackboard

In 1825, Michael Faraday discovered one of the most fascinating compounds in chemistry: benzene. While isolating the components of oily residues of illuminating gas, Faraday identified a mysterious liquid, with a peculiar aromatic smell, which would go on to transform the landscape of chemistry.

Within the pages of the Philosophical Transactions of the Royal Society of London, Faraday described this seemingly simple yet profoundly unique molecule. What set benzene apart, even in its earliest discovery, was its resistance to easy chemical classification. Its peculiar behaviour, such as its surprising stability despite being highly unsaturated, hinted at a deeper mystery that would not be fully resolved until the mid-19th century with the proposal of its cyclic structure.

Benzene’s physical properties only added to its mystique. This colourless liquid emitted a faintly sweet, intoxicating aroma – a hallmark of aromatic compounds. With a boiling point of 80.1°C, it was volatile and highly flammable, making it both a chemical curiosity and a potential industrial tool. Early chemists were captivated by its ability to dissolve fats, oils and other nonpolar substances, which made it a valuable solvent for experimentation and industrial processes. Yet, it was benzene’s chemical properties – its reactivity and stability – that would become the cornerstone of an entire branch of organic chemistry: aromatic compounds.

Today, benzene is everywhere, interwoven into the structures of more complex molecules that enhance our daily lives in fields as diverse as health, energy, advanced materials, electronics, food, dyes and biotechnology. This humble molecule opened the doors to a vast universe of aromatic compounds and an endless array of applications that have redefined our world.

Stability and tunability

Following benzene’s legacy came polycyclic aromatic hydrocarbons (PAHs), a fascinating class of organic molecules composed of fused benzene rings. These structures not only preserve benzene’s aromatic stability, thanks to their electron delocalisation, but also exhibit unique electronic and optical properties determined by their size and arrangement. While smaller PAHs, like naphthalene and anthracene, had been characterised in the 19th century, the discovery of larger, more complex systems unveiled entirely new and surprising properties – from discrete energy levels in simpler molecules to semiconducting behaviours in larger systems like pentacene.

The synthesis and study of these compounds paved the way for nanographenes, opening new dimensions in chemistry and materials science. Through meticulous control over their molecular structures, researchers have learned to design advanced materials with tunable properties, such as electron conductivity, fluorescence, chirality and chemical reactivity. This painstaking precision highlights the intrinsic beauty of chemistry at its most fundamental level, an art of exactitude that continues to push the boundaries of possibility.

A landmark achievement in this journey was the discovery of hexabenzocoronene (HBC), in 1958. This molecule, composed of 42 carbon atoms forming 13 hexagonal rings in a perfectly flat structure, remained the largest fully characterised polycyclic aromatic hydrocarbon for decades. Yet the creativity of organic chemistry knows no bounds. Klaus Müllen, a pioneer in the exploration of nanographenes, succeeded in 2002 in synthesising a remarkable structure formed by 222 carbon atoms with a diameter of 3nm, demonstrating the immense potential of organic synthesis to construct tailor-made graphene molecules.

Graphene stands out as the ultimate expression of benzene’s versatility

The fusion of benzene rings has given rise to some of the most remarkable materials in modern science, including fullerenes and carbon nanotubes. Fullerenes, often referred to as buckyballs, are spherical molecules composed entirely of carbon atoms arranged in a pattern of hexagons and pentagons, resembling a molecular soccer ball. These structures, discovered in 1985, owe their stability and symmetry to the aromaticity derived from benzene-like rings. Similarly, carbon nanotubes – long, cylindrical structures composed of fused aromatic rings – have captivated scientists with their extraordinary strength, flexibility and electrical conductivity. Both fullerenes and nanotubes exemplify the limitless potential of carbon chemistry, with benzene as the foundational building block.

Among these innovations, graphene stands out as the ultimate expression of benzene’s versatility. This two-dimensional material, consisting of a single layer of carbon atoms arranged in a honeycomb lattice, is essentially a sheet of fused benzene rings. Graphene’s remarkable properties – its transparency, strength, flexibility and electrical conductivity – have earned it the title of a ‘gift of gods’. Graphene, like benzene before it, has the power to revolutionise multiple fields, from electronics and energy storage to medicine and materials science.

Beyond its scientific impact, benzene holds a special place in education. Generations of high school and university students have been introduced to the elegance of its structure and the profound mystery surrounding its stability. The study of benzene serves as an accessible entry point for understanding broader concepts like aromaticity, resonance and molecular orbitals. By celebrating the bicentennial of its discovery, we honour not only the legacy of Faraday but also the enduring role of benzene in inspiring curiosity, innovation and the next generation of chemists.

To celebrate the 200th anniversary of benzene’s discovery and its extraordinary legacy, the Royal Society of Chemistry will release a thematic special issue, uniting several RSC journals in a collaborative tribute to benzene’s unparalleled influence.

This special issue, edited by Ben Feringa and Nazario Martín, will illuminate the enduring relevance of benzene by exploring its far-reaching legacy in carbon-based systems, from the fundamental concepts of aromaticity and antiaromaticity to groundbreaking research on polycyclic aromatic hydrocarbons (PAHs), molecular nanographenes (via both top-down and bottom-up approaches), graphene and its derivatives, carbon nanotubes and fullerenes. It will also delve into cutting-edge developments from (anti)aromatic compounds synthesised through on-surface methodologies to benzene-based molecular machines.

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