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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Zahn, Stefan Birckner, Eckhard Grummt, Ulrich-walter Fleischhauer, Jan Görls, Helmar Beckert, Rainer |
| Description | Author Affiliation: Fleischhauer J ( Ruprecht-Karls-University Heidelberg, Department of Chemistry, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany. j.fleischhauer@oci.uni-heidelberg.de) |
| Abstract | Pentacene and its derivatives are among the most important examples of π-electron-rich molecules used in organic field effect transistors. The replacement of CH groups by nitrogen atoms opens an elegant way to generate highly electron-deficient molecules, known as oligoazaacenes. We describe the synthesis and spectroscopic properties of two novel derivatives of this family, namely the zwitterionic and quinoidal conjugated forms of dihydro-5,6,7,12,13,14-hexaazapentacene (fluorubine). We outline a powerful strategy to tune the electronic properties of these redox-active azaacenes by the selective introduction of substituted pyrazines. Their acidochromic and solvatochromic behaviour is investigated experimentally and interpreted with the help of theoretical calculations. The simple “exchange” of substituents or protonation is shown to significantly alter the spectroscopic and electronic properties of these remarkably stable π-systems. Their exceptional optical properties, such as high fluorescence quantum yields combined with a redox-active behaviour, make them promising candidates for sensor materials. Additional marked features in the solid state, such as herringbone packing in combination with short π–π distances, will open access to electronic materials. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 15 |
| Volume Number | 18 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2012-04-10 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Aza Compounds Chemistry Coloring Agents Heterocyclic Compounds Naphthacenes Chemical Synthesis Pyrazines Crystallography, X-Ray Models, Molecular Molecular Structure Quantum Theory Research Support, Non-U.S. Gov't |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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