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Stable and Easily Accessible Functional Dyes: Dihydrotetraazaanthracenes as Versatile Precursors for Higher Acenes
Author(s) -
Gampe Dominique Mario,
Kaufmann Martin,
Jakobi Dörthe,
Sachse Torsten,
Presselt Martin,
Beckert Rainer,
Görls Helmar
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500230
Subject(s) - chemistry , molecule , absorption (acoustics) , condensation , absorption spectroscopy , mesoionic , density functional theory , spectroscopy , computational chemistry , single crystal , fluorescence , block (permutation group theory) , combinatorial chemistry , crystallography , organic chemistry , materials science , physics , quantum mechanics , composite material , thermodynamics , geometry , mathematics
A series of new dihydrotetraazaanthracenes and one new dihydrotetraazatetracene as substances for applications in organoelectronic devices and as suitable building blocks for higher azaacenes was synthesised. The condensation of aromatic diamines with dichlorodicyanopyrazine led to these tricyclic/tetracyclic compounds. Syntheses of N ‐substituted phenylenediamines were developed to enable the introduction of multiple functional groups such as ester, amino, or nitro groups on the chromophoric system. Relationships between the structure and the spectroscopic properties could be derived from UV/Vis absorption and fluorescence spectroscopy, as well as by DFT and TD‐DFT calculations of molecular and aggregate structures. The absorption spectra are dominated by π–π* transitions of the single molecules, whereas aggregation needs to be taken into account to obtain reasonable agreement between theory and experiment in certain cases. Single‐crystal X‐ray analyses were carried out to examine the morphology and solid packing effects. Finally, a dihydrotetraazaanthracene was used as a building‐block to create a mesoionic octaazapentacene.