Communication
Organic & Biomolecular Chemistry
Research Program of Chinese Academy of Sciences
(XDB12010400) for financial support.
Notes and references
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Fig. 5 HOMO and LUMO of 5a–5c calculated by the B3LYP/6-31G (d)
method.
systems. The band gaps of 5a–c from the DFT calculations
were 2.20, 2.05, and 2.08 eV, respectively, which was similar to
the results from UV-Vis absorption (2.05, 1.92, and 1.95 eV).
Furthermore, both calculation and experimental results
showed that the HOMO–LUMO gaps of 5b and 5c were higher
than that of hexacene (1.84 eV),1b but lower than those of
pentacene (2.1 eV)13 and HBP (2.67 eV),9a which could make
5b and 5c have the potential to be narrow bandgap materials.
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Conclusions
In summary, we have conveniently synthesized a new type of
acenes, dinaphtho[8,1,2-cde:2′,1′,8′-uva]pentacene derivative 5c
and its analogues 5a and 5b from commercial material. These
new acene derivatives showed good stabilities and solubilities
in various organic solvents. It was also found that molecule 5c
has
a twisted configuration, but showed obvious inter-
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molecular π-stacking interactions in the solid state. The UV-Vis
spectra, CV and DFT calculations further showed that 5b and
5c have stronger electronic delocalization and smaller
bandgap than that of HBP with a similar twisted structure. It
can be expected that this new type of acenes with specific
structures and properties could find potential applications in
organic functional materials, and this is currently being
investigated.
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Acknowledgements
We thank the National Natural Science Foundation of China
(21272264, 21332008), the National Basic Research Program
(2011CB932501, 2015CB856502), and the Strategic Priority
Org. Biomol. Chem.
This journal is © The Royal Society of Chemistry 2015