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Synthetic Strategies for Oligoynes
Author(s) -
Jevric Martyn,
Nielsen Mogens Brøndsted
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402261
Subject(s) - chemistry , conjugated system , steric effects , combinatorial chemistry , triple bond , redox , phosphine , molecule , nanotechnology , carbon fibers , catalysis , organic chemistry , polymer , double bond , materials science , composite number , composite material
Oligoynes with alternating carbon–carbon single and triple bonds and with suitable end groups are interesting compounds for materials science and molecular electronics. Here we present recent synthetic strategies for the preparation of oligoynes as well as a few oligoenynes, in both linear and cyclic scaffolds, with different end groups, which are present either to incorporate additional functionality and properties to the molecule (such as redox properties) or to sterically shield the oligoyne chain. The strategies involve a variety of metal‐catalyzed reactions as well as procedures in which the oligoyne is prepared in the final step of the synthesis from related conjugated precursors. End‐capping of terminal alkynes with phosphine‐gold(I) complexes presents a way to enhance the stability and has been used not only to construct oligoynes, but also cyclic radiaannulene structures from stable and isolable tetraethynylethene building blocks (see frontispiece); upon ready reduction, these cyclic enynes can form cumulenic structures.