Abstract: Crystallization control of organic conjugated small molecules is in high demand for the engineering of functional materials in organic optoelectronics. Here, we report solution additive-assisted crystallization of a model non-planar aromatic hydrocarbon derivative 9,10-diphenylanthracene. Among the studied series of related aromatic hydrocarbons comprising pyrene, perylene, anthracene, tetracene, and rubrene, only tetracene revealed clear reproducible effects allowing one to perform selective crystallization of metastable 9,10-diphenylanthracene polymorphs. Additionally, crystallization of 9,10-diphenylanthracene and pyrene produced a stoichiometric co-crystal (PYR–DPA) having a segregated layered molecular packing with alternating 9,10-diphenylanthracene and pyrene layers. Remarkably, the molecular packing of pyrene within the co-crystal is unique and represented by the herringbone motif, whereas the molecular packing in known pyrene polymorphs is represented by π-stacked molecules. The co-crystal also demonstrated a bright photoluminescence with a photoluminescence quantum yield of 51%. Considering the morphology of 9,10-diphenylanthracene crystals obtained and crystal structures of PYR–DPA co-crystal and tetracene, we have proposed the mechanism of additive-assisted polymorphism based on the inhibition of (111) facet of α-DPA and promoting of the layered structure crystallization corresponding to metastable polymorphs (β- and γ-DPA). We highlight the additive-assisted crystallization approach as a powerful tool for the crystal engineering of functional materials for organic optoelectronics.

Cite: Sonina A.A. , Cheshkina D.S. , Kazantsev M.S.
Additive-Assisted Crystallization of 9,10-Diphenylanthracene
Crystals. 2023. V.13. N6. P.861. DOI: 10.3390/cryst13060861 WOS РИНЦ

Dates:

Submitted:	Apr 22, 2023
Accepted:	May 22, 2023
Published print:	May 24, 2023

Identifiers:

Web of science	WOS:001014305100001
Elibrary	61585358
OpenAlex	W4378223470

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