Hexakis(trimethylsilylethynyl)[3]radialene: A Carbon‐Rich Chromophore with Unusual Electronic Properties

1995/04/13 by Tim Lange, Völker Gramlich, Walter Amrein +4 · 2 citations
Chemistry · Engineering · #Synthesis and Properties of Aromatic Compounds #Synthesis and characterization of novel inorganic/organometallic compounds #Molecular Junctions and Nanostructures

paper · doi:10.1002/anie.199508051

openalex publication_date 1995/04/13 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/29

Abstract

Hexaethynyl[3]radialene (1 a) is isoelectronic and isosteric with the known hexacyano[3]radialene and a molecular precursor for a two-dimensional all-carbon network. The hexakis(trimethylsilyl) derivative 1 b was now prepared by addition of tetrachlorocyclopropene to deprotonated 1,5-bis(trimethylsilyl)penta-1,4-diyne, followed by oxidation, and was characterized by X-ray crystallography. In solution, 1 b shows an unexpected purple-red color and is reduced in two reversible one-electron steps to the violet radical anion 1 b and dianion 1 b2−.

Citations

• The molecular structure of trimethylenecyclopropane
• Preparation and Properties, Reactions, and Applications of Radialenes
• Tris(fluoren‐9‐ylidene)cyclopropane, a Novel [3]Radialene
• Negatively substituted trimethylenecyclopropane dianions
• Polyanthraquinocyclopropanes, dianthraquinocyclopropanone, and dianthraquinoethylene. Synthesis and properties

Cited by

• Triarylamines on [3]Radialene Scaffold: Novel [3]Radialene-based, Multistep, Wide-range Redox Systems with Remarkably Low Oxidation Potentials
• Radialene [wikipedia]