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. 2021 Oct 22;26(21):6391.
doi: 10.3390/molecules26216391.

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

Roman Linko  1 , Michael Ryabov  1 , Pavel Strashnov  1 , Pavel Dorovatovskii  2 , Victor Khrustalev  1   3 , Victor Davydov  1
Affiliations

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

Roman Linko et al. Molecules. .

Abstract

Understanding the interactions of organic donor and acceptor molecules in binary associates is crucial for design and control of their functions. Herein, we carried out a theoretical study on the properties of charge transfer complexes of 1,3,6-trinitro-9,10-phenanthrenequinone (PQ) with 23 aromatic π-electron donors. Density functional theory (DFT) was employed to obtain geometries, frontier orbital energy levels and amounts of charge transfer in the ground and first excited states. For the most effective donors, namely, dibenzotetrathiafulvalene, pentacene, tetrathiafulvalene, 5,10-dimethylphenazine, and tetramethyl-p-phenylenediamine, the amount of charge transfer in the ground state was shown to be 0.134-0.240 e-. Further, a novel charge transfer complex of PQ with anthracene was isolated in crystalline form and its molecular and crystal structure elucidated by single-crystal synchrotron X-ray diffraction.

Keywords: 1,3,6-trinitro-9,10-phenanthrenequinone; DFT; X-ray diffraction; anthracene; charge transfer complex.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Configurations of acceptor PQ, one of the donors MC, and two possible CTCs [PQ-MC] and [PQ-MC]’.
Figure 2
Figure 2
HOMO-LUMO energy levels for complexes of PQ with AN and TMDA according to DFT calculations.
Figure 3
Figure 3
X-ray crystallographic structure of PQ and AN in complex I.
Figure 4
Figure 4
Crystal structure of complex I. (a) View along crystallographic a axis; (b) view along crystallographic b axis; (c) view along crystallographic c axis.
See this image and copyright information in PMC

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