Developing organic-based functional materials for optoelectronics offers diverse potential for new devices that can be thinly constructed, low power consuming, tunable, and flexible. Moreover, designed self-assembly in these materials can offer functional complexity with relatively less resource input in synthesis. Donor-acceptor columnar liquid crystals (DACLCs) area a class of materials that consist of electron-rich aromatic donors interacting with electron-poor aromatic acceptor molecules. These complementary components self-assemble into alternating column structures with π-orbital overlap between adjacent molecules that results in charge-transfer (CT), leading to interesting optical properties and potential semiconducting behavior. Here we present the synthesis of new molecular components for DACLC materials aimed at tailoring their bulk properties for novel applications.  Specifically, synthesis and incorporation of remarkably high-energy-HOMO phenanthrazine (PAZ) donors with different aromatic acceptors explores the potential for DACLCs as stable NIR absorbing materials. Related, the synthesis of 3,6-bis(thiophen-2-yl)diketopyrrolopyrrole (TDPP) and its use as both a primary donor <i>or</i> acceptor component in DACLCs will be discussed.  In addition to the mixed donor/acceptor potential of TDPP for a variety of new DACLC materials, the incorporation of sulfur (3p orbitals) into the π-orbital overlap of DACLCs is shown to enhance CT excitation in general. The temperature dependent phase behavior and optical properties of new DACLCs incorporating the PAZ and/or TDPP components will be discussed, as well as their potential for the generation of, and control over, stable NIR CT absorption and charge mobility.

Developing molecular components for enhanced optoelectronic function in charge-transfer liquid crystals

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