Abstract
A series of five thionated naphthalene diimides (NDIs) with linear alkyl chains was synthesized and the optoelectronic, self-assembly, and device properties were studied.
Highlights
We recently showed that thionation leads to an increase in thin film transistor electron mobility by two orders of magnitude when the four diimide oxygens are replaced with four sulfurs in perylene diimide (PDI) small molecules.[33]
Unlike the series of branched chain PDIs and naphthalene diimides (NDIs), we find that the electron mobility does not increase appreciably with degree of thionation, and the average mobilities are quite consistent ranging from 3.9 Â 10À2 to 7.4 Â 10À2 cm[2] VÀ1 sÀ1 for one to three sulfurs
The previous report suggests that the inability to synthesize the S4 compound may be due to the low LUMO energy of the S3 decreasing its reactivity towards Lawesson’s reagent;[32] our results suggest that further thionation is, possible
Summary
While there have been significant advances in the design of p-conjugated p-type materials for organic electronics over the last 20 years, research on complementary n-type materials has gained interest only recently.[1,2,3,4,5] High-mobility p-conjugated n-type materials are needed for use as acceptor materials in organic photovoltaics (OPVs) and in n-channel organic thin-film transistors (OTFTs).[6,7,8,9,10,11,12] As with OPVs, there are many more examples of p-type (i.e. hole transporting) OTFTs than n-type (i.e. electron transporting).[13,14,15] Design criteria for new p-conjugated n-type materials for transistor applications include (1) lowering the LUMO level for efficient electron injection and (2) invoking strong intermolecular interactions for efficient electron transport in the solid-state.[16,17]We recently showed that thionation leads to an increase in thin film transistor electron mobility by two orders of magnitude when the four diimide oxygens are replaced with four sulfurs in PDI small molecules.[33]. We were interested in expanding the scope of the thionation reaction to smaller NDIs, as well as replacing the branched 3-hexylundecyl side chain used in the PDI study with a linear alkyl chain so that the solid-state packing and self-assembly properties could be studied
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
