10.1021/jo015810n.s001
Yuming Zhao
Yuming
Zhao
Katie Campbell
Katie
Campbell
Rik R. Tykwinski
Rik R.
Tykwinski
Iterative Synthesis and Characterization of Cross-Conjugated
Iso-Polydiacetylenes
American Chemical Society
2001
oligomer
Si
nonamer 19
triflate
UV
2001-11-15 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Iterative_Synthesis_and_Characterization_of_Cross-Conjugated_Iso-Polydiacetylenes/3691665
An iterative synthesis of cross-conjugated iso-polydiacetylenes (iso-PDAs) is reported based on three
fundamental building blocks: vinyl triflates <b>8</b>, <b>9</b>, and <b>25</b>. An efficient sequence of palladium-catalyzed cross-coupling reactions of vinyl triflates and terminal alkynes has been employed to
extend the chain length of these oligomers. The longest member of the series, nonamer <b>19</b>, spans
3.4 nm from Si to Si atom. The stability and solubility of the conjugated oligomers have been
evaluated as a function of pendant substitution. Assessment of solid-state structural properties
was achieved via X-ray crystallographic analyses of monomer <b>12</b> and trimer <b>14</b>. The electronic
characteristics of the monodisperse oligomers have been fully analyzed by UV−vis spectroscopy in
solution and as thin films, and these studies suggest that π-electron communication is present
along the enyne framework, but quickly reaches saturation by the stage of nonamer <b>19</b>.