End-functionalization of dithiarubicene: modulation of optoelectronic properties by metal-catalyzed coupling reactions and device application
Journal of Materials Chemistry C, ISSN: 2050-7526, Vol: 9, Issue: 18, Page: 5920-5929
2021
- 4Citations
- 3Captures
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Article Description
In order to modulate the optoelectronic properties of dithiarubicene (DTR) by end-functionalization and reveal the structure-property relationship in detail, we have carried out a set of metal-catalyzed coupling reactions. Electron-withdrawing cyano (CN-DTR) and pyridyl (Py-DTR) groups, electron-donating methoxy (MeO-DTR) and thienyl (Th-DTR) groups, and relatively electron-neutral trimethylsilylethynyl (Ethynyl-DTR) group were introduced on theDTRcore by using halogenatedDTRderivatives as precursors. Particularly, we could successfully introduce the methoxy group by CuO-catalyzed reactions in high yield. As a result of the combination of the electron-acceptingDTRcore and the electron-donating methoxy group, the UV-Vis-NIR absorption spectrum ofMeO-DTRshowed a large red-shift of the peak maximum by approximately 90 nm. In addition, the introduction of substituents made it possible to finely tune the HOMO and LUMO energy levels ofDTRthereby enabling its application in OFET devices. Thanks to the elevated HOMO energy level, the OFET device based onMeO-DTRexhibited a hole mobility (μ) of up to 1.4 × 10cmVs. On the other hand, the device based onCN-DTRhad an ambipolar characteristic, which exhibited a moderate electron mobility (μ= 1.1 × 10cmVs) due to its low-lying LUMO energy level. From the XRD measurements,MeO-DTRandCN-DTRwere found to adopt an edge-on molecular orientation on the HMDS-treated SiOsubstrate.
Bibliographic Details
Royal Society of Chemistry (RSC)
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