The first representative of a new class of charge transfer complexes in o-quinone series for organic semiconductors

The first representative of a new class of charge transfer complexes for organic semiconductors was synthesized. The reaction of p-nitroaniline (PNA) with [1,10]-phenanthroline-5,6-dione (PD) results in the formation of a stable molecular charge transfer (CT) complex PNA3-PD2 in a ratio of 3:2. The structure of the molecular CT complex PNA3-PD2 was established by X-ray diffraction studies. Using the density functional theory method, it is shown that several types of intermolecular interactions are realized in the complex: between the PNA amino group and the nitro group of another PNA molecule, carbonyl groups, and PD nitrogen atoms. Complex PNA3-PD2 is stable only in solid form. The diffuse reflectance UV–vis spectrum of PNA3-PD2 crystal powder is characterized by the intense weakly structured long-wavelength absorption band up to 650 nm. Quantum chemical calculations of the electronic structure have shown that the complex PNA3-PD2 is a straight-band semiconductor with a band gap of 2.11 eV. [Display omitted] •The first example of a new class of charge transfer complexes (CTC) in o-quinone series.•The CTC is stable only in solid form and is a straight-band semiconductor.•It has a structure PNA3-PD2 (PNA, p-nitroaniline; PD, phenanthroline-5,6-dione).•X-ray and theoretical studies of the interactions in the layered structure of CTC.•An effective approach to creating novel organic materials.