Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 21, Pages 4697-4703Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob00987a
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Funding
- ERATO program from JST [JPMJER1302]
- Funding Program for KAKENHI from MEXT [16 K05771, JP26288093, JP15 K13816]
- JSPS
- World Premier International Research Center (WPI) Initiative, Japan
- Grants-in-Aid for Scientific Research [16K05771, 16H02285, 17H05149] Funding Source: KAKEN
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The synthesis and properties of a new pi-extended double [6] helicene 2 and a dithia[6] helicene 3 are described. Compared to the previously reported parent double-helicene molecule 1, the introduction of n-butyl groups successfully improved the solubility, which allowed an experimental investigation into the electronic structure of 2 and 3 by photophysical measurements and cyclic voltammetry. The characteristic two-blade propeller structures of 2 and 3 were unambiguously determined by single-crystal X-ray diffraction analysis. The crystal packing structure of 2 exhibited a contorted two-dimensional stacking, whereby molecules of n-pentane were incorporated in the stacks. Despite the presence of n-butyl groups, 3 formed a unique three-dimensional stacking lattice in the crystal. Time-resolved microwave conductivity measurements revealed that the double helicenes (1-3) exhibited transient conductivities. An organic field-effect transistor fabricated using 3 was found to function as a p-type transistor.
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