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Verfasst von:Geib, Sonja [VerfasserIn]   i
 Martens-Kruck, Susanne [VerfasserIn]   i
 Lombeck, Florian [VerfasserIn]   i
 Wadepohl, Hubert [VerfasserIn]   i
 Gade, Lutz H. [VerfasserIn]   i
Titel:1,3,6,8-tetraazapyrenes
Titelzusatz:synthesis, solid-state structures, and properties as redox-active materials
Verf.angabe:Sonja Geib, Susanne C. Martens, Ute Zschieschang, Florian Lombeck, Hubert Wadepohl, Hagen Klauk, and Lutz H. Gade
E-Jahr:2012
Jahr:June 25, 2012
Umfang:10 S.
Fussnoten:Gesehen am 26.04.2018
Titel Quelle:Enthalten in: The journal of organic chemistry
Ort Quelle:[S.l.] : American Chemical Society, 1936
Jahr Quelle:2012
Band/Heft Quelle:77(2012), 14, Seite 6107-6116
ISSN Quelle:1520-6904
Abstract:A series of new tetraazapyrene (TAPy) derivatives has been synthesized by reducing 1,4,5,8-tetranitronaphthalene to its corresponding tin salt (I) and reacting it with perfluorinated alkyl or aryl anhydrides. The resulting 2,7-disubstituted TAPy molecules and the known parent compound 1,3,6,8-tetraazapyrene (II) have been further derivatized by core chlorination and bromination. The brominated compounds served as starting materials for Suzuki cross-coupling reactions with electron-poor arylboronic acids. Single-crystal X-ray analyses established polymorphism for some TAPy compounds. The ground-state geometries of all new TAPy derivatives were modeled with DFT methods [B3PW91/6-31 g(d,p) and B3PW91/6-311+g(d,p)], especially focusing on the energies of the lowest unoccupied molecular orbital (LUMO) and the electron affinities (EA) of the molecules. The results of the calculations were confirmed experimentally by cyclic voltammetry to evaluate the substitution effects at the 2 and 7 position and the core positions, respectively, and gave LUMO energy levels that range from −3.57 to −4.14 eV. Fabrication of organic field-effect transistors (OFETs) with several of these tetraazapyrenes established their potential as organic n-type semiconductors.
DOI:doi:10.1021/jo300894p
URL:Bitte beachten Sie: Dies ist ein Bibliographieeintrag. Ein Volltextzugriff für Mitglieder der Universität besteht hier nur, falls für die entsprechende Zeitschrift/den entsprechenden Sammelband ein Abonnement besteht oder es sich um einen OpenAccess-Titel handelt.

Volltext: http://dx.doi.org/10.1021/jo300894p
 Volltext: https://doi.org/10.1021/jo300894p
 DOI: https://doi.org/10.1021/jo300894p
Datenträger:Online-Ressource
Sprache:eng
K10plus-PPN:1572394242
Verknüpfungen:→ Zeitschrift

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