From Hexaphenylbenzene to 1,2,3,4,5,6-Hexacyclohexylcyclohexane.
Marcel DillenburgerZijie QiuCheng-Wei JuBeate MüllerSvenja MorsbachDieter SchollmeyerAkimitsu NaritaKlaus MüllenPublished in: Journal of the American Chemical Society (2020)
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.
Keyphrases
- high performance liquid chromatography
- mass spectrometry
- high resolution
- tandem mass spectrometry
- gas chromatography
- simultaneous determination
- solid phase extraction
- liquid chromatography
- capillary electrophoresis
- epithelial mesenchymal transition
- particulate matter
- solid state
- magnetic resonance
- ms ms
- room temperature
- magnetic resonance imaging