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Dicyanopolyynes: A Homologuous Series of End‐Capped Linear sp Carbon
Author(s) -
Schermann Günther,
Grösser Thomas,
Hampel Frank,
Hirsch Andreas
Publication year - 1997
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19970030718
Subject(s) - carbyne , carbon chain , regioselectivity , chemistry , series (stratigraphy) , carbon fibers , computational chemistry , stereochemistry , organic chemistry , materials science , composite material , composite number , paleontology , carbene , biology , catalysis
Abstract The synthesis, isolation, spectroscopic characterization, and computational investigations of the rod‐shaped dicyanopolyynes 1–6 (C 2 n N 2 , n = 4–9), which are model substances for the hypothetical one‐dimensional carbon allotrope carbyne sp‐C ∞ , are described. Based on the trends in the spectroscopic behavior of 1–6 with increasing chain length, the electronic as well as the NMR properties of carbyne are predicted. For the investigation of the synthetic potential of this compound class, a first selected series of regioselective derivatizations is presented with the synthesis of the [4+2] and [3+2] cycloadducts 7–12 .