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. 2019 Nov 18;25(64):14522-14526.
doi: 10.1002/chem.201903646. Epub 2019 Oct 18.

N-Acenoacenes

Lukas Ahrens  1 , Sebastian Hahn  1 , Frank Rominger  1 , Jan Freudenberg  1   2 , Uwe H F Bunz  1   3
Affiliations

N-Acenoacenes

Lukas Ahrens et al. Chemistry. .

Abstract

The syntheses of new, fourfold alkynylated tetraazaacenoacenes (tetraazaanthracenoanthracene, tetraazatetracenotetracene and tetraazapentacenopentacene) are reported. This novel heteroacenoacene motif exhibits surprisingly strong electronic coupling between its constituting diazaacene units.

Keywords: 2D acenes; aromaticity; azaacenes; electronic coupling; semiconductors.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of tetrabenzoheptacene A and heptacene B.[ 2 , 3 ]
Scheme 1
Scheme 1
Buchwald–Hartwig coupling of the N‐acenoacenes 3 a–c by using diamines 2 a–c and triflates 1 a,b. [a] RuPhos Pd G1 (10 mol %), cesium carbonate (6.0 equiv), toluene, 110 °C, 24 h.
Figure 2
Figure 2
Photographs of 3 a–c (from left to right) under daylight (left) and UV light (right, λ ex=365 nm) in CH2Cl2.
Figure 3
Figure 3
Top: Normalized absorption spectra of 3 a–c in CH2Cl2. Bottom: 3 c, 4 c and 5 c in CH2Cl2.
Figure 4
Figure 4
Acenes 4 a–c, [17] N‐acenoacenes 3 a–c, and N‐heterophenes 5 a–c. [18]
Figure 5
Figure 5
NICS(1) values of compounds 3 a–c, 4 a–c, and 5 a–c (B3LYP/6‐311++G** level); TMS groups were used instead of TIPS.
Figure 6
Figure 6
Solid‐state structures of 3 a and 3 b; distances between neighboring molecules; visualization of overlap and packing.
See this image and copyright information in PMC

References

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