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- W2000687069 abstract "Abstract The synthesis of 2,3‐R 2 ‐9,10‐(OMe) 2 ‐substituted pentacenes (R=OMe, F, Br, CN; 1 – 4 ) from 2,3‐R 2 ‐9,10‐dimethoxy‐6,13‐dihydro‐6,13‐ethanopentacene‐15,16‐diones (α‐diketone‐bridged precursors) by photochemically induced bis‐decarbonylation (Strating–Zwanenburg reaction) is described. Under matrix‐isolation conditions (solid Ar, 10 K) the S 1 transitions of 1 and 2 undergo hypsochromic and those of 3 and 4 bathochromic shifts compared to parent pentacene. The S 1 transition wavelengths correlate well with the difference of substituent parameters σ p . A computational analysis of the excited states at the CAM‐B3LYP/6‐311+G** level of theory provides an assignment of the electronic transitions. Photolysis in solution at room temperature yields red [R=OMe ( 1 )], blue [R=Br ( 3 ), F ( 2 )], and green [R=CN ( 4 )] pentacenes. The compounds are oxygen‐sensitive and have low solubility, but their formation can be monitored by UV/Vis and, in the case of R=CN, also by 1 H NMR spectroscopy. The S 1 transition in 4 does not show the typical pentacene fine structure in the electronic absorption spectrum. Photogeneration in the presence of oxygen leads to a number of photoproducts that could be identified by monitoring the reaction by 1 H NMR spectroscopy for R=OMe." @default.
- W2000687069 created "2016-06-24" @default.
- W2000687069 creator A5015977477 @default.
- W2000687069 creator A5041020064 @default.
- W2000687069 date "2012-01-02" @default.
- W2000687069 modified "2023-10-18" @default.
- W2000687069 title "The Influence of Terminal Push-Pull Substitution on the Electronic Structure and Optical Properties of Pentacenes" @default.
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- W2000687069 doi "https://doi.org/10.1002/chem.201101036" @default.
- W2000687069 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/22213393" @default.
- W2000687069 hasPublicationYear "2012" @default.
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