Toward carbyne: Synthesis and stability of really long polyynes

Tykwinski R, Chalifoux W, Eisler S, Lucotti A, Tommasini M, Fazzi D, Del Zoppo M, Zerbi G (2010)

Publication Type: Journal article, Original article

Publication year: 2010

Journal

Pure and Applied Chemistry International Union of Pure and Applied Chemistry

Original Authors: Tykwinski R.R., Chalifoux W., Eisler S., Lucotti A., Tommasini M., Fazzi D., Del Zoppo M., Zerbi G.

Publisher: International Union of Pure and Applied Chemistry

Book Volume: 82

Pages Range: 891-904

Journal Issue: 4

DOI: 10.1351/PAC-CON-09-09-04

Abstract

Molecules composed of sp-hybridized carbon chains (polyynes) are the simplest of the known conjugated organic oligomers. In comparison to their counterparts such as polyacetylene and polydiacetylene, however, the formation of polyynes has traditionally posed a difficult synthetic challenge. In particular, there is no reliable method to form end-capped polyethynylene, and monodisperse polyynes have therefore been assembled. As a result, structure-property relationships for shorter polyynes have been relatively well established in recent years, while extension of these trends toward longer polyynes has remained a difficult task. Using the Fritsch-Buttenberg-Wiechell (FBW) rearrangement, the formation of diynes through decaynes has become possible and has provided a unique chance to explore the physical characteristics of conjugated polyyne chains. This paper highlights recent advances in the synthesis of extended polyynes, as well as interesting aspects of their NMR, Raman, and UV/vis spectroscopic analyses. These synthetic achievements offer the opportunity to predict some of the properties of the carbon allotrope carbyne. In particular, a set of X-ray crystallo - graphic analyses of t-Bu end-capped polyynes (tBu[n]) shows a definitive experimental trend in reduced bond-length alternation (BLA). © 2010 IUPAC.

Authors with CRIS profile

Rik Tykwinski Lehrstuhl für Organische Chemie I

Involved external institutions

Politecnico di Milano IT Italy (IT) Italian Institute of Technology / Istituto Italiano di Tecnologia (IIT) IT Italy (IT) University of New Brunswick (UNB) CA Canada (CA) University of Alberta CA Canada (CA)

How to cite

APA:

Tykwinski, R., Chalifoux, W., Eisler, S., Lucotti, A., Tommasini, M., Fazzi, D.,... Zerbi, G. (2010). Toward carbyne: Synthesis and stability of really long polyynes. Pure and Applied Chemistry, 82(4), 891-904. https://doi.org/10.1351/PAC-CON-09-09-04

MLA:

Tykwinski, Rik, et al. "Toward carbyne: Synthesis and stability of really long polyynes." Pure and Applied Chemistry 82.4 (2010): 891-904.

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