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Crystal structure and luminescence properties of 2-[(2′,6′-dimeth­oxy-2,3′-bipyridin-6-yl)­oxy]-9-(pyridin-2-yl)-9H-carbazole

In the title com­pound, C(29)H(22)N(4)O(3), the carbazole system forms a dihedral angle of 68.45 (3)° with the mean plane of the bi­pyridine ring system. The bi­pyridine ring system, with two meth­oxy substituents, is approximately planar (r.m.s. deviation = 0.0670 Å), with a dihedral angle of 7.91 ...

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Autores principales: Moon, Suk-Hee, Park, Ki-Min, Kim, Jinho, Kang, Youngjin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6829735/
https://www.ncbi.nlm.nih.gov/pubmed/31709084
http://dx.doi.org/10.1107/S2056989019013549
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author Moon, Suk-Hee
Park, Ki-Min
Kim, Jinho
Kang, Youngjin
author_facet Moon, Suk-Hee
Park, Ki-Min
Kim, Jinho
Kang, Youngjin
author_sort Moon, Suk-Hee
collection PubMed
description In the title com­pound, C(29)H(22)N(4)O(3), the carbazole system forms a dihedral angle of 68.45 (3)° with the mean plane of the bi­pyridine ring system. The bi­pyridine ring system, with two meth­oxy substituents, is approximately planar (r.m.s. deviation = 0.0670 Å), with a dihedral angle of 7.91 (13)° between the planes of the two pyridine rings. Intra­molecular C—H⋯O/N hydrogen bonds may promote the planarity of the bipyridyl ring system. In the pyridyl-substituted carbazole fragment, the pyridine ring is tilted by 56.65 (4)° with respect to the mean plane of the carbazole system (r.m.s. deviation = 0.0191 Å). In the crystal, adjacent mol­ecules are connected via C—H⋯O/N hydrogen bonds and C—H⋯π inter­actions, resulting in the formation of a three-dimensional (3D) supra­molecular network. In addition, the 3D structure contains inter­molecular π–π stacking inter­actions, with centroid–centroid distances of 3.5634 (12) Å between pyridine rings. The title com­pound exhibits a high energy gap (3.48 eV) and triplet energy (2.64 eV), indicating that it could be a suitable host material in organic light-emitting diode (OLED) applications.
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spelling pubmed-68297352019-11-08 Crystal structure and luminescence properties of 2-[(2′,6′-dimeth­oxy-2,3′-bipyridin-6-yl)­oxy]-9-(pyridin-2-yl)-9H-carbazole Moon, Suk-Hee Park, Ki-Min Kim, Jinho Kang, Youngjin Acta Crystallogr E Crystallogr Commun Research Communications In the title com­pound, C(29)H(22)N(4)O(3), the carbazole system forms a dihedral angle of 68.45 (3)° with the mean plane of the bi­pyridine ring system. The bi­pyridine ring system, with two meth­oxy substituents, is approximately planar (r.m.s. deviation = 0.0670 Å), with a dihedral angle of 7.91 (13)° between the planes of the two pyridine rings. Intra­molecular C—H⋯O/N hydrogen bonds may promote the planarity of the bipyridyl ring system. In the pyridyl-substituted carbazole fragment, the pyridine ring is tilted by 56.65 (4)° with respect to the mean plane of the carbazole system (r.m.s. deviation = 0.0191 Å). In the crystal, adjacent mol­ecules are connected via C—H⋯O/N hydrogen bonds and C—H⋯π inter­actions, resulting in the formation of a three-dimensional (3D) supra­molecular network. In addition, the 3D structure contains inter­molecular π–π stacking inter­actions, with centroid–centroid distances of 3.5634 (12) Å between pyridine rings. The title com­pound exhibits a high energy gap (3.48 eV) and triplet energy (2.64 eV), indicating that it could be a suitable host material in organic light-emitting diode (OLED) applications. International Union of Crystallography 2019-10-22 /pmc/articles/PMC6829735/ /pubmed/31709084 http://dx.doi.org/10.1107/S2056989019013549 Text en © Moon et al. 2019 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/
spellingShingle Research Communications
Moon, Suk-Hee
Park, Ki-Min
Kim, Jinho
Kang, Youngjin
Crystal structure and luminescence properties of 2-[(2′,6′-dimeth­oxy-2,3′-bipyridin-6-yl)­oxy]-9-(pyridin-2-yl)-9H-carbazole
title Crystal structure and luminescence properties of 2-[(2′,6′-dimeth­oxy-2,3′-bipyridin-6-yl)­oxy]-9-(pyridin-2-yl)-9H-carbazole
title_full Crystal structure and luminescence properties of 2-[(2′,6′-dimeth­oxy-2,3′-bipyridin-6-yl)­oxy]-9-(pyridin-2-yl)-9H-carbazole
title_fullStr Crystal structure and luminescence properties of 2-[(2′,6′-dimeth­oxy-2,3′-bipyridin-6-yl)­oxy]-9-(pyridin-2-yl)-9H-carbazole
title_full_unstemmed Crystal structure and luminescence properties of 2-[(2′,6′-dimeth­oxy-2,3′-bipyridin-6-yl)­oxy]-9-(pyridin-2-yl)-9H-carbazole
title_short Crystal structure and luminescence properties of 2-[(2′,6′-dimeth­oxy-2,3′-bipyridin-6-yl)­oxy]-9-(pyridin-2-yl)-9H-carbazole
title_sort crystal structure and luminescence properties of 2-[(2′,6′-dimeth­oxy-2,3′-bipyridin-6-yl)­oxy]-9-(pyridin-2-yl)-9h-carbazole
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6829735/
https://www.ncbi.nlm.nih.gov/pubmed/31709084
http://dx.doi.org/10.1107/S2056989019013549
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