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Skonieczny K, Gryko DT. Light-Induced Direct Arylation in the Solid Crystalline State as a Strategy Towards π-Expanded Imidazoles. Chem Asian J. 2016;11(18):2513-7doi: 10.1002/asia.201600752.
Skonieczny, K., & Gryko, D. T. (2016). Light-Induced Direct Arylation in the Solid Crystalline State as a Strategy Towards π-Expanded Imidazoles. Chemistry, an Asian journal, 11(18), 2513-7. https://doi.org/10.1002/asia.201600752
Skonieczny, Kamil, and Gryko, Daniel T. "Light-Induced Direct Arylation in the Solid Crystalline State as a Strategy Towards π-Expanded Imidazoles." Chemistry, an Asian journal vol. 11,18 (2016): 2513-7. doi: https://doi.org/10.1002/asia.201600752
Skonieczny K, Gryko DT. Light-Induced Direct Arylation in the Solid Crystalline State as a Strategy Towards π-Expanded Imidazoles. Chem Asian J. 2016 Sep 20;11(18):2513-7. doi: 10.1002/asia.201600752. Epub 2016 Aug 25. PMID: 27452918.
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Chem Asian J. 2016 Sep 20;11(18):2513-7. doi: 10.1002/asia.201600752. Epub 2016 Aug 25.

Light-Induced Direct Arylation in the Solid Crystalline State as a Strategy Towards π-Expanded Imidazoles.

Chemistry, an Asian journal

Kamil Skonieczny, Daniel T Gryko

Affiliations

  1. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44-52, 01-224, Warsaw, Poland.
  2. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44-52, 01-224, Warsaw, Poland. [email protected].

PMID: 27452918 DOI: 10.1002/asia.201600752

Abstract

π-Expanded imidazoles bearing the 2-iodophenyl substituent at position 2 undergo direct photoinduced intramolecular arylation in the solid, crystalline state leading to large non-planar heterocycles. An analogous reaction employing 2-bromophenyl and 2-chlorophenyl substituents is considerably slower. Such processes have never before been demonstrated to occur in crystals and have allowed the efficient synthesizes of structurally unique compounds containing either the phenanthro[9',10':4,5]imidazo[1,2-f]phenanthridine moiety or structurally related skeletons. The reaction occurs in the thin crystalline layers irradiated with UV photons in an almost quantitative manner over 48-72 h. Several previously unknown architectures have been prepared using this methodology. Furthermore, the optical properties of these π-expanded imidazoles can be altered with the addition of heteroatoms and/or electron-donating groups.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: arylation; fluorescence; fused-ring systems; nitrogen heterocycles; photochemistry

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