Charge Transfer Complexes of 1,3,6-Trinitro-9,10-phenanthrenequinone with Polycyclic Aromatic Compounds

Area of Science:

• Organic Chemistry
• Materials Science
• Computational Chemistry

Background:

• Understanding organic donor-acceptor interactions is key for designing functional materials.
• Charge transfer complexes play a vital role in various electronic and optical applications.

Purpose of the Study:

• To theoretically investigate the properties of charge transfer complexes formed by 1,3,6-trinitro-9,10-phenanthrenequinone (PQ) with 23 aromatic π-electron donors.
• To determine the extent of charge transfer and analyze electronic properties in ground and excited states.
• To experimentally validate findings through structural elucidation of a novel complex.

Main Methods:

• Density Functional Theory (DFT) calculations were used to model molecular geometries and electronic structures.
• Frontier orbital energy levels and charge transfer amounts were computed.
• Single-crystal synchrotron X-ray diffraction was employed for structural analysis of an isolated complex.

Main Results:

• The study identified specific aromatic donors exhibiting significant charge transfer with PQ, ranging from 0.134 to 0.240 e⁻ in the ground state.
• Key effective donors included dibenzotetrathiafulvalene, pentacene, tetrathiafulvalene, 5,10-dimethylphenazine, and tetramethyl-p-phenylenediamine.
• A novel charge transfer complex of PQ with anthracene was successfully synthesized, isolated, and its crystal structure determined.

Conclusions:

• The theoretical and experimental findings provide valuable insights into the structure-property relationships of PQ-based charge transfer complexes.
• This research contributes to the rational design of organic materials with tailored electronic and optical functionalities.
• The characterization of the PQ-anthracene complex offers a foundation for further investigations into similar systems.