Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2021 Mar 8;27(14):4553-4556.
doi: 10.1002/chem.202004761. Epub 2021 Feb 17.

Diazapentacenes from Quinacridones

Thomas Wiesner  1 , Lukas Ahrens  1 , Frank Rominger  1 , Jan Freudenberg  1 , Uwe H F Bunz  1
Affiliations

Diazapentacenes from Quinacridones

Thomas Wiesner et al. Chemistry. .

Abstract

Bis(silylethynylated) 5,7- and 5,12-diazapentacenes were synthesized from cis- and trans-quinacridone using protection, alkynylation and deoxygenation. The solid-state packing of the targets is determined by choice and position of the silylethynyl substituents. The position of the substituents and nitrogen atoms influence the optical properties of the targets.

Keywords: azaacenes; photostability; quinacridines; semiconductors; solid-state packing.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interests.

Figures

Scheme 1
Scheme 1
Synthetic route towards diazapentacenes 1 a,b. Synthesis of 2 a,b is carried out accordingly (Scheme S1).
Figure 1
Figure 1
Structures of diazaacenes (quinacridines) 1 and 2 and regioisomeric diazapentacenes 3 and 3′.
Figure 2
Figure 2
a) Normalized absorption spectra of 1 a, 2 a and 3 in n‐hexane. b) Stability of 1 b in DCM under ambient light and atmosphere. c) Stability of 2 b in DCM under ambient light and atmosphere.
Figure 3
Figure 3
At high concentrations 2 b reacts via thermally allowed [4+2] cycloaddition forming the dimer 9.
Figure 4
Figure 4
Solid state packing of 1  a,b and 2  a,b.
See this image and copyright information in PMC

References

    1. None
    1. Labana S. S., Labana L. L., Chem. Rev. 1967, 67, 1–18;
    1. Eckert A., Seidel F., J. Prakt. Chem. 1921, 102, 338–360.
    1. None
    1. Lincke G., Dyes Pigment. 2000, 44, 101–122;

LinkOut - more resources