|Solubility in water||insoluble|
|Related compounds||Ethyne (monomer)|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Polyacetylene (IUPAC name: polyethyne) is an organic polymer with the repeating unit (C2H2)n. The high electrical conductivity discovered for these polymers led to intense interest in the use of organic compounds in microelectronics (organic semiconductors). The discovery of the high conductivity of polyacetylene by Hideki Shirakawa, Alan J. Heeger, and Alan G MacDiarmid was recognized by the Nobel Prize in Chemistry in 2000.
Structure of polyacetylene
One distinguishes trans-polyacetylene, with all double bonds in the trans configuration, from cis-polyactylene, with all double bonds in the cis configuration. Each hydrogen atom can be replaced by a functional group.
Interest in the conductive properties of oxidatively doped polyacetylenes was ignited in the mid 1970s with the discovery of a silvery, conductive polyacetylene by Hideki Shirakawa. He polymerized acetylene with 1000 times the amount of catalyst normally used when performing the reaction. Shirakawa later collaborated with physicist Alan J. Heeger and chemist Alan G MacDiarmid, discovering in 1976 that oxidation of this material with iodine results in a 108-fold increase in conductivity. The conductivity of this doped material can approach the conductivity of the best available conductor, silver. The three were awarded the Nobel Prize in Chemistry in 2000 for their discoveries.
Polyacetylene is generally not prepared by polymerizing acetylene because of the violence of its uncontrolled polymerization. The most common syntheses use ring opening metathesis polymerisation ("ROMP") of molecules like cyclooctatetraene and substituted derivatives thereof.
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