Two new cases of polymorphism in diagonally substituted rubrene derivatives

Margaret L. Clapham; Christopher J. Douglas

doi:10.1107/S2056989023002736

Two new cases of polymorphism in diagonally substituted rubrene derivatives

Margaret L. Clapham, Christopher J. Douglas

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

Abstract

The crystal structures of two rubrene derivatives, 5,11-diphenyl-6,12-bis[4-(trifluoromethyl)phenyl]tetracene, C₄₄H₂₆F₆, and 5,11-bis(4-tert-butylphenyl)-6,12-diphenyltetracene, C₅₀H₄₄, are presented. Each are substituted on diagonal (5/11) phenyl rings. Each derivative has one polymorph reported previously. A discussion of the differences between each derivative and its previously reported polymorph is provided. The triclinic packing of the CF₃-substituted structure is similar to the packing of the parent rubrene’s triclinic polymorph. In the tertbutyl-substituted structure, a planar tetracene core formed, which has been hypothesized but never published. Crystallization conditions are provided as they differ from previous reports.

Original language	English (US)
Pages (from-to)	406-409
Number of pages	4
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	79
Issue number	Pt 4
DOIs	https://doi.org/10.1107/S2056989023002736
State	Published - Mar 31 2023

Bibliographical note

Funding Information:
XRD experiments were conducted at the X-ray Crystallographic Laboratory at the University of Minnesota with the help of Dr Victor G. Young Jr. Instrumentation was purchased with a grant from the National Science Foundation (CHE-1229400). We also thank the reviewer for their thoughtful comments and suggestions.

Publisher Copyright:
© 2023 International Union of Crystallography. All rights reserved.

Keywords

crystal structure
polymorphism
rubrene

PubMed: MeSH publication types

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title = "Two new cases of polymorphism in diagonally substituted rubrene derivatives",

abstract = "The crystal structures of two rubrene derivatives, 5,11-diphenyl-6,12-bis[4-(trifluoromethyl)phenyl]tetracene, C44H26F6, and 5,11-bis(4-tert-butylphenyl)-6,12-diphenyltetracene, C50H44, are presented. Each are substituted on diagonal (5/11) phenyl rings. Each derivative has one polymorph reported previously. A discussion of the differences between each derivative and its previously reported polymorph is provided. The triclinic packing of the CF3-substituted structure is similar to the packing of the parent rubrene{\textquoteright}s triclinic polymorph. In the tertbutyl-substituted structure, a planar tetracene core formed, which has been hypothesized but never published. Crystallization conditions are provided as they differ from previous reports.",

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author = "Clapham, {Margaret L.} and Douglas, {Christopher J.}",

note = "Funding Information: XRD experiments were conducted at the X-ray Crystallographic Laboratory at the University of Minnesota with the help of Dr Victor G. Young Jr. Instrumentation was purchased with a grant from the National Science Foundation (CHE-1229400). We also thank the reviewer for their thoughtful comments and suggestions. Publisher Copyright: {\textcopyright} 2023 International Union of Crystallography. All rights reserved.",

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N1 - Funding Information: XRD experiments were conducted at the X-ray Crystallographic Laboratory at the University of Minnesota with the help of Dr Victor G. Young Jr. Instrumentation was purchased with a grant from the National Science Foundation (CHE-1229400). We also thank the reviewer for their thoughtful comments and suggestions. Publisher Copyright: © 2023 International Union of Crystallography. All rights reserved.

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N2 - The crystal structures of two rubrene derivatives, 5,11-diphenyl-6,12-bis[4-(trifluoromethyl)phenyl]tetracene, C44H26F6, and 5,11-bis(4-tert-butylphenyl)-6,12-diphenyltetracene, C50H44, are presented. Each are substituted on diagonal (5/11) phenyl rings. Each derivative has one polymorph reported previously. A discussion of the differences between each derivative and its previously reported polymorph is provided. The triclinic packing of the CF3-substituted structure is similar to the packing of the parent rubrene’s triclinic polymorph. In the tertbutyl-substituted structure, a planar tetracene core formed, which has been hypothesized but never published. Crystallization conditions are provided as they differ from previous reports.

AB - The crystal structures of two rubrene derivatives, 5,11-diphenyl-6,12-bis[4-(trifluoromethyl)phenyl]tetracene, C44H26F6, and 5,11-bis(4-tert-butylphenyl)-6,12-diphenyltetracene, C50H44, are presented. Each are substituted on diagonal (5/11) phenyl rings. Each derivative has one polymorph reported previously. A discussion of the differences between each derivative and its previously reported polymorph is provided. The triclinic packing of the CF3-substituted structure is similar to the packing of the parent rubrene’s triclinic polymorph. In the tertbutyl-substituted structure, a planar tetracene core formed, which has been hypothesized but never published. Crystallization conditions are provided as they differ from previous reports.

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Two new cases of polymorphism in diagonally substituted rubrene derivatives

Abstract

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