Design of High-Performance Organic Semiconductors by Intra- and Intermolecular Charge Transfer Interaction.

Charge transfer (CT) interactions have rarely been used to organize supramolecules and cross-linked objects. However, the ever-increasing understanding of CT interactions opens up new avenues for the design of innovative materials with tailored electronic properties. Herein, several molar ratios of highly crystalline π-conjugated n%TCNQ@Sq-1,6Py oligomers (n equal molar ratio of tetracyanoquinodimethane (TCNQ) to 1,6-diaminopyrene (1,6Py) moiety) with simultaneously stable intra- and intermolecular CT mechanisms are prepared. As a result, the π-conjugated 200%TCNQ@Sq-1,6Py CT complex indicates stable intra- and intermolecular CT interactions resulting in extremely high electrical conductivity of 8.7 × 10-2 S cm-1 at room temperature, a charge-distance capacitance of 70.62 F g-1 at the current density of 0.625 A g-1 which significantly increases to 968.7 F g-1 by doping of polyaniline (PANI) at a current density of 0.312 A g-1. Finally, it exhibits a capacitance retention of 70% of the initial specific capacitance after 1000 cycles at room temperature. This type of π-conjugated oligomer CT complex can be used to improve existing CT-based energy storage devices, such as capacitors.