A family of novel highly π-extended tetracyano-substituted acene diimides, named as tetracyanodiacenaphthoanthracene diimides (TCDADIs), have been synthesized using a facile four-fold Knoevenagel condensation strategy. Unlike conventional cyano substitution reactions, our approach enables access to a large π-conjugated backbone with the in-situ formation of four cyano substitutents at room temperature while avoiding extra cyano-functionalization reactions. TCDADIs decorated with different N-alkyl substituents present good solubility, near-coplanar backbones, good crystallinity, and low-lying lowest unoccupied molecular orbital energies of -4.33 eV, all of which contribute to desirable electron-transport performance when applied in organic field-effect transistors (OFET). The highest electron mobility of an OFET based on a 2-hexyldecyl-substituted TCDADI single crystal reaches 12.6 cm2 V-1 s-1 , which is not only among the highest values for the reported n-type organic semiconductor materials (OSMs) but also exceeds that of most n-type OSMs decorated with imide units.
Keywords: Acene Diimides; Electron Transport; Organic Field-Effect Transistors; n-Type Organic Semiconductors.
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