期刊
JOURNAL OF MATERIALS CHEMISTRY C
卷 3, 期 2, 页码 283-290出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4tc02164a
关键词
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资金
- MEXT, Japan [23245041, 25.1759]
- Japan Society for the Promotion of Science (JSPS)
- Grants-in-Aid for Scientific Research [13J01759] Funding Source: KAKEN
Dibenzo[a,e]pentalene-embedded thienoquinoidals with dicyanomethylene termini were synthesized as new pi-extended thienoquinoidals for n-type organic semiconductors. Single crystal X-ray analysis demonstrated that the target molecule has an all trans-polyene structure with reasonable bond-length alternation in the thienoquinoidal strand, indicative of effective extension of the pi-conjugation system. Thanks to their pi-extended structures, not just the low-lying LUMO energy levels (-4.2 to -4.3 eV) but also relatively high HOMO energy levels (similar to-5.6 eV) were characterized by means of cyclic voltammetry. Interestingly, depending on the position of the solubilizing long alkyl groups, they formed H- or J-aggregate-like structures in the thin-film state testified by the thin film absorption spectra. These distinct intermolecular interactions in the thin film state could cause different behaviours in thin-film field-effect transistors; for the former ambipolar characteristics were observed, whereas only n-type response was detected for the latter.
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