Reduction of bis(benzothiadiazol) by LiAlH4/CuI gives diethynylated diaminobenzoquinoneimine. This building block accesses novel targets in a one-step condensation reaction with different ortho-quinones, resulting in unexpected rearrangement products. The compounds are characterized by their photophysical and electrochemical data as well as quantum chemical calculations.
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http://dx.doi.org/10.1039/c5cc05427c | DOI Listing |
Chemistry
November 2021
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
The synthesis of novel (N-)acene-based cyclooligomers is reported. Glaser-Hay coupling of the bisethynylated monomers results in cyclodimers and cyclotrimers that are separable by column and gel-permeation chromatographies. For the diazatetracene, the use of sec-butyl-silylethynyl groups is necessary to achieve solubility.
View Article and Find Full Text PDFChemistry
June 2018
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
The synthesis of bisalkynylated derivatives of tetrabenzo[a,c,p,r]heptacene and tetrabenzo[a,c,l,n]pentacene via two-/fourfold Stille reactions involving a 9-stannafluorene and suitable tetrabromoacenes is reported. These triphenylene-"winged" heptacenes are surprisingly stable and maintain a significant portion of the electronic properties of heptacenes.
View Article and Find Full Text PDFChemistry
July 2017
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
The synthesis and optical properties of several novel fluorescent and/or phosphorescent bridged tolanes (tolanophanes) are reported and their optical and structural properties are investigated. Specifically, diiodinated and bisalkynylated tolanophanes were obtained, and characterized by spectroscopy and computational methods. They represent attractive building blocks for novel polymers and emissive solid-state materials.
View Article and Find Full Text PDFJ Am Chem Soc
May 2017
Department of Chemistry, University of Rochester, Rochester, New York 14627, United States.
Iron-catalyzed cross-coupling reactions using alkynyl nucleophiles represent an attractive approach for the incorporation of alkynyl moieties into organic molecules. In the present study, a multitechnique approach combining inorganic spectroscopic methods, inorganic synthesis, and reaction studies is applied to iron-SciOPP catalyzed alkynyl-alkyl cross-couplings, providing the first detailed insight into the effects of variation from sp- to sp-hybridized nucleophiles on iron speciation and reactivity. Reaction studies demonstrate that reaction of FeBr(SciOPP) with 1 equiv (triisopropylsilyl)ethynylmagnesium bromide (TIPS-CC-MgBr) leads to a distribution of mono-, bis-, and tris-alkynylated iron(II)-SciOPP species due to rapid alkynyl ligand redistribution.
View Article and Find Full Text PDFChem Commun (Camb)
October 2015
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
Reduction of bis(benzothiadiazol) by LiAlH4/CuI gives diethynylated diaminobenzoquinoneimine. This building block accesses novel targets in a one-step condensation reaction with different ortho-quinones, resulting in unexpected rearrangement products. The compounds are characterized by their photophysical and electrochemical data as well as quantum chemical calculations.
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