Roles of 3-Ethylrhodanine in Attaining Highly Ordered Crystal Arrays of Ambipolar Diketopyrrolopyrrole Oligomers.

Abstract

Until now, only limited DPP oligomers delivered ambipolar semiconductor characteristics. To develop a facile strategy of preparing ambipolar mono-DPP oligomers, two dithienyl diketopyrrolopyrrole (DPPT) based-conjugated molecules, DPPT-RD and DPPT-DCV, which contain 3-ethylrhodanine (RD) and dicyano-2-vinyl (DCV) end substituents were synthesized. The influences of the -RD end substituents on the molecular properties, solid-state morphology, and OFET performances of the DPPT oligomer were investigated. The UV-vis absorption and CV results showed that the RD end substituents provide the DPPT oligomer suitable EHOMO and ELUMO for hole and electron injection from the Au source-drain electrodes. Moreover, the RD end substituents also improve the crystalline nature of the DPPT oligomer. That is, DPPT-RD can form crystal arrays with good lattice orientation, larger crystalline size, and without polymorphism. With those properties, DPPT-RD thus display ambipolar characteristic with μh and μe reaching 2.16 × 10-2 and 7.27 × 10-2 cm2 V-1 s-1, respectively.