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Hexakis(trimethylsilylethynyl)[3]radialene: A Carbon‐Rich Chromophore with Unusual Electronic Properties
Author(s) -
Lange Tim,
Gramlich Volker,
Amrein Walter,
Diederich François,
Gross Maurice,
Boudon Corinne,
Gisselbrecht JeanPaul
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199508051
Subject(s) - trimethylsilyl , deprotonation , chromophore , chemistry , derivative (finance) , carbon fibers , ion , photochemistry , medicinal chemistry , polymer chemistry , organic chemistry , materials science , composite number , composite material , financial economics , economics
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 b 2− .