Open AccessCyclic polyacetylene
Author(s) -
Zhihui Miao,
Stella A. Gonsales,
Christian Ehm,
Frédéric Mentink-Vigier,
Clifford R. Bowers,
Brent S. Sumerlin,
Adam S. Veige
Publication year - 2021
Publication title -
nature chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 9.996
H-Index - 232
eISSN - 1755-4349
pISSN - 1755-4330
DOI - 10.1038/s41557-021-00713-2
Subject(s) - polyacetylene , chemistry , annulene , topology (electrical circuits) , catalysis , acetylene , polymerization , tungsten , polymer , polymer chemistry , combinatorial chemistry , crystallography , stereochemistry , organic chemistry , combinatorics , mathematics
Here we demonstrate the synthesis of cyclic polyacetylene (c-PA), or [∞]annulene, via homogeneous tungsten-catalysed polymerization of acetylene. Unique to the cyclic structure and evidence for its topology, the c-PA contains >99% trans double bonds, even when synthesized at -94 °C. High activity with low catalyst loadings allows for the synthesis of temporarily soluble c-PA, thus opening the opportunity to derivatize the polymer in solution. Absolute evidence for the cyclic topology comes from atomic force microscopy images of bottlebrush derivatives generated from soluble c-PA. Now available in its cyclic form, initial characterization studies are presented to elucidate the topological differences compared with traditionally synthesized linear polyacetylene. One advantage to the synthesis of c-PA is the direct synthesis of the trans-transoid isomer. Low defect concentrations, low soliton concentration, and relatively high conjugation lengths are characteristics of c-PA. Efficient catalysis permits the rapid synthesis of lustrous flexible thin films of c-PA, and when doped with I 2 , they are highly conductive (398 (±76) Ω -1 cm -1 ).