From Hexaphenylbenzene to 1,2,3,4,5,6-Hexacyclohexylcyclohexane | Zendy

Marcel Dillenburger | Zendy; Zijie Qiu | Zendy; ChengWei Ju | Zendy; Beate Müller | Zendy; Svenja Morsbach | Zendy; Dieter Schollmeyer | Zendy; Akimitsu Narita | Zendy; Kläus Müllen | Zendy

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From Hexaphenylbenzene to 1,2,3,4,5,6-Hexacyclohexylcyclohexane

Author(s) -

Marcel Dillenburger,

Zijie Qiu,

ChengWei Ju,

Beate Müller,

Svenja Morsbach,

Dieter Schollmeyer,

Akimitsu Narita,

Kläus Müllen

Publication year - 2020

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.0c04956

Subject(s) - chemistry , cyclohexane , molecule , mass spectrometry , crystal structure , crystallography , organic chemistry , chromatography

The hydrogenation of hexaphenylbenzene was studied, affording novel partially hydrogenated hexacyclohexylbenzene ( HCB ) as well as fully hydrogenated 1,2,3,4,5,6-hexacyclohexylcyclohexane ( HCC ) as an unprecedented "oligocyclohexyl" molecule. The reaction process was analyzed by mass spectrometry with atmospheric pressure chemical ionization and high-performance liquid chromatography. From a crude product mixture, two different crystals with flake- and block-shapes could be grown and analyzed by X-ray crystallography, revealing their structures as HCB and HCC . While a geared arrangement of cyclohexyl substitutes was found in HCB , two isomeric structures were identified in HCC crystal with chair and twist-boat conformations of the central cyclohexane.

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