chemistry

Hexacene

Hexacene is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Hexacene rather than just read about it. In short: Hexacene is an aromatic compound consisting of six linearly-fused benzene rings. It is a blue-green, air-stable solid with low solubility.

Key takeaways

Hexacene belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Hexacene to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Hexacene from memory before moving on to harder problems.

Reference excerpt

Hexacene is an aromatic compound consisting of six linearly-fused benzene rings. It is a blue-green, air-stable solid with low solubility. Hexacene is one of a series of linear polycyclic molecules created by such aromatic ring fusions, a series termed acenes; the previous in the series is pentacene (with five fused rings) and the next is heptacene (with seven). It and other acenes and their derivatives have been investigated in potential applications related to organic semiconductors. Like larger acenes, hexacene is poorly soluble, but derivatives have been prepared with improved solubility, such as 6,15-Bis(tri-t-butylsilylethynyl)hexacene, which melts with decomposition at 96 °C.

Syntheses and structure Hexacene has been the subject of many syntheses. One route uses thermal decarbonylation of a monoketone precursor.

Further reading First synthesis: Marschalk, C. Linear hexacenes. Bull. Soc. Chim. Fr. 6, 1112–1121 (1939). E. Clar (1939). "Hexacen, ein grüner, einfacher Kohlenwasserstoff (Aromatische Kohlenwasserstoffe, XXIV. Mitteil) (trans=Hexacene, a Green Simple Hydrocarbon (Aromatic hydrocarbons. XXIV.)". Ber. Dtsch. Chem. Ges. B. 72B: 1817–1821. doi:10.1002/cber.19390721002. E. Clar (1942). "Eine neue Synthese des Hexacens (Aromatische Kohlenwasserstoffe, XXXIV. Mitteil)". Berichte der deutschen chemischen Gesellschaft. 75 (11): 1283–1287. doi:10.1002/cber.19420751102. By dehydrogenation of hexacosahydrohexacene by palladium on carbonBailey, W.J.; Liao, C.W. (1955). "Cyclic Dienes. XI. New Syntheses of Hexacene and Heptacene". J. Am. Chem. Soc. 77 (4): 992–993. doi:10.1021/ja01609a055. Isolation: Angliker H.; Rommel E.; Wirz J. (1982). "Electronic spectra of hexacene in solution (ground state, triplet state, dication and dianion)". Chemical Physics Letters. 87 (2): 208–12. Bibcode:1982CPL....87..208A. doi:10.1016/0009-2614(82)83589-6. By decarbonylation of a diketone precursor:Mondal, R.; Adhikari, R.M.; Shah, B.K.; Neckers, D.C. (2007). "Revisiting the Stability of Hexacenes". Org. Lett. 9 (13): 2505–2508. doi:10.1021/ol0709376. PMID 17516652. Deoxygenation route: Krüger, Justus; Eisenhut, Frank; Alonso, José M.; Lehmann, Thomas; Guitián, Enrique; Pérez, Dolores; Skidin, Dmitry; Gamaleja, Florian; Ryndyk, Dmitry A.; Joachim, Christian; Peña, Diego; Moresco, Francesca; Cuniberti, Gianaurelio (2017). "Imaging the electronic structure of on-surface generated hexacene". Chem. Commun. 53 (10): 1583–1586. doi:10.1039/C6CC09327B. ISSN 1359-7345. PMID 27990553.

External links Molecular graphics representation of the X-ray crystallographic structure determined for 6,15-bis(tri-t-butylsilylethynyl)hexacene—hexacene with bulky, protective substituents in the reactive 6- and 15- ring positions, see rotating graphic at base of page. Sander-Wise Polycyclic Aromatic Hydrocarbon Structure Index entry for hexacene, NIST Special Publication 922.

References

Illustrations

Worked examples

Example 1 — a first encounter with Hexacene

Start with the simplest possible case. Write down what Hexacene claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Hexacene before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Hexacene ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Hexacene

In research: Hexacene appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Hexacene in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Hexacene is common in secondary-school and first-year university syllabi. It links to neighbouring topics Acenes, Hexacyclic compounds, Organic semiconductors, so understanding it makes those chapters shorter.
In everyday life: Look for Hexacene outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Hexacene in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Hexacene means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Hexacene out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Hexacene in simple terms?

Hexacene is an aromatic compound consisting of six linearly-fused benzene rings. It is a blue-green, air-stable solid with low solubility.

Why does Hexacene matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Hexacene?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Hexacene.