Additive-Assisted Crystallization of 9,10-Diphenylanthracene
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...
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MDPI AG
2023-05-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/13/6/861 |
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| author | Alina A. Sonina Darya S. Cheshkina Maxim S. Kazantsev |
| author_facet | Alina A. Sonina Darya S. Cheshkina Maxim S. Kazantsev |
| author_sort | Alina A. Sonina |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-11T02:36:19Z |
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| id | doaj.art-eff9d35be54a49e7a27c153d5b91e2e6 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-11T02:36:19Z |
| publishDate | 2023-05-01 |
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| record_format | Article |
| series | Crystals |
| spelling | doaj.art-eff9d35be54a49e7a27c153d5b91e2e62023-11-18T09:55:48ZengMDPI AGCrystals2073-43522023-05-0113686110.3390/cryst13060861Additive-Assisted Crystallization of 9,10-DiphenylanthraceneAlina A. Sonina0Darya S. Cheshkina1Maxim S. Kazantsev2Organic Electronics Laboratory, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, RussiaOrganic Electronics Laboratory, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, RussiaOrganic Electronics Laboratory, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, RussiaCrystallization 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.https://www.mdpi.com/2073-4352/13/6/861additive-assisted crystallizationpolymorphismconjugated small moleculesorganic semiconductorsorganic electronics |
| spellingShingle | Alina A. Sonina Darya S. Cheshkina Maxim S. Kazantsev Additive-Assisted Crystallization of 9,10-Diphenylanthracene Crystals additive-assisted crystallization polymorphism conjugated small molecules organic semiconductors organic electronics |
| title | Additive-Assisted Crystallization of 9,10-Diphenylanthracene |
| title_full | Additive-Assisted Crystallization of 9,10-Diphenylanthracene |
| title_fullStr | Additive-Assisted Crystallization of 9,10-Diphenylanthracene |
| title_full_unstemmed | Additive-Assisted Crystallization of 9,10-Diphenylanthracene |
| title_short | Additive-Assisted Crystallization of 9,10-Diphenylanthracene |
| title_sort | additive assisted crystallization of 9 10 diphenylanthracene |
| topic | additive-assisted crystallization polymorphism conjugated small molecules organic semiconductors organic electronics |
| url | https://www.mdpi.com/2073-4352/13/6/861 |
| work_keys_str_mv | AT alinaasonina additiveassistedcrystallizationof910diphenylanthracene AT daryascheshkina additiveassistedcrystallizationof910diphenylanthracene AT maximskazantsev additiveassistedcrystallizationof910diphenylanthracene |