Acenes , or polyacenes, are a class of organic compounds and polycyclic aromatic hydrocarbons consisting of linearly attached benzene rings [1] .
Representatives of the class with a large number of rings have the potential for use in optoelectronics and are actively studied in chemistry and electrical engineering . For example, in pentacene , involved in organic field effect transistors , the mobility of charge carriers reaches 5 cm 2 / V; the compound is the best organic p-type semiconductor [2] .
| Title | Chemical formula | Number of rings | Molar mass , g / mol | CAS Number | Structural formula |
|---|---|---|---|---|---|
| Benzene | C 6 H 6 | one | 78.11 |  | |
| Naphthalene | C 10 H 8 | 2 | 128.17 |  | |
| Anthracene | C 14 H 10 | 3 | 178.23 |  | |
| Tetracene | C 18 H 12 | four | 228.29 |  | |
| Pentacene | C 22 H 14 | five | 278.35 |  | |
| Hexacene | C 26 H 16 | 6 | 328.41 |  | |
| Heptacene | C 30 H 18 | 7 | 378.46 |  |
The last two indicated acenes in the table — hexacene and heptacene — are very reactive, which is why they were obtained due to matrix isolation [3] .
Senior Representatives
Older representatives of acenes are also known, that is, with a large number of rings in their composition [4] , which are used in the process of obtaining nanotubes and graphene . Unsubstituted octacen and nonacen were found in matrix isolation [2] . The first reports of stable derivatives of nonacene indicate that, due to the electronic effects of thioaryl substituents, the compound — nonacene — is not a , but a closed-shell system with the lowest energy difference between, which has ever been reported for acenes [5] - this observation goes against the rule of Kashi . Subsequent studies of various derivatives, including the study of crystalline structures, did not have any such contradictions [6] . In 2017, decacen was obtained [7] .
See also
Notes
- ↑ IUPAC Gold Book internet edition: " Acenes ".
- ↑ 1 2 Tönshoff C. , Bettinger HF Photogeneration of octacene and nonacene. (English) // Angewandte Chemie (International ed. in English). - 2010 .-- Vol. 49, no. 24 . - P. 4125-4128. - DOI : 10.1002 / anie.200906355 . - PMID 20432492 .
- ↑ Anthony JE The larger acenes: versatile organic semiconductors. (English) // Angewandte Chemie (International ed. in English). - 2008 .-- Vol. 47, no. 3 . - P. 452-483. - DOI : 10.1002 / anie.200604045 . - PMID 18046697 .
- ↑ Zade SS , Bendikov M. Heptacene and beyond: the longest characterized acenes. (English) // Angewandte Chemie (International ed. in English). - 2010 .-- Vol. 49, no. 24 . - P. 4012-4015. - DOI : 10.1002 / anie.200906002 . - PMID 20468014 .
- ↑ Kaur I. , Jazdzyk M. , Stein NN , Prusevich P. , Miller GP Design, synthesis, and characterization of a persistent nonacene derivative. (Eng.) // Journal of the American Chemical Society. - 2010 .-- Vol. 132, no. 4 . - P. 1261-1263. - DOI : 10.1021 / ja9095472 . - PMID 20055388 .
- ↑ Purushothaman B. , Bruzek M. , Parkin SR , Miller AF , Anthony JE Synthesis and structural characterization of crystalline nonacenes. (English) // Angewandte Chemie (International ed. in English). - 2011. - Vol. 50, no. 31 . - P. 7013-7017. - DOI : 10.1002 / anie.201102671 . - PMID 21717552 .
- ↑ Dekatsen • Arkady Kuramshin • Scientific picture of the day on the “Elements” • Chemistry