Green and Rapid Hydrothermal Crystallization and Synthesis of Fully Conjugated Aromatic Compounds

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2018
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Taublaender, M. Josef
Glöcklhofer, Florian
Marchetti-Deschmann, Martina
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Angewandte Chemie International Edition. Wiley-Blackwell - STM. 2018, 57(38), pp. 12270-12274. ISSN 0570-0833. eISSN 1521-3773. Available under: doi: 10.1002/anie.201801277
Zusammenfassung

Highly fused, fully conjugated aromatic compounds are interesting candidates for organic electronics. With higher crystallinity their electronic properties improve. It is shown here that the crystallization of three archetypes of such molecules-pentacenetetrone, indigo, and perinone-can be achieved hydrothermally. Given their molecular structure, this is a truly startling finding. In addition, it is demonstrated that perinone can also be synthesized in solely high-temperature water from the starting compounds naphthalene bisanhydride and o-phenylene diamine without the need for co-solvents or catalysts. The transformation can be drastically accelerated by the application of microwave irradiation. This is the first report on the hydrothermal generation of two fused heterocycles.

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540 Chemie
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carbonyl dyes, crystalline materials, fused heterocycles, green chemistry, hydrothermal synthesis
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ISO 690TAUBLAENDER, M. Josef, Florian GLÖCKLHOFER, Martina MARCHETTI-DESCHMANN, Miriam M. UNTERLASS, 2018. Green and Rapid Hydrothermal Crystallization and Synthesis of Fully Conjugated Aromatic Compounds. In: Angewandte Chemie International Edition. Wiley-Blackwell - STM. 2018, 57(38), pp. 12270-12274. ISSN 0570-0833. eISSN 1521-3773. Available under: doi: 10.1002/anie.201801277
BibTex
@article{Taublaender2018-09-17Green-55236,
  year={2018},
  doi={10.1002/anie.201801277},
  title={Green and Rapid Hydrothermal Crystallization and Synthesis of Fully Conjugated Aromatic Compounds},
  number={38},
  volume={57},
  issn={0570-0833},
  journal={Angewandte Chemie International Edition},
  pages={12270--12274},
  author={Taublaender, M. Josef and Glöcklhofer, Florian and Marchetti-Deschmann, Martina and Unterlass, Miriam M.}
}
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