0000000001308781
AUTHOR
Junzhi Liu
Unexpected Scholl Reaction of 6,7,13,14-Tetraarylbenzo[k]tetraphene: Selective Formation of Five-Membered Rings in Polycyclic Aromatic Hydrocarbons
Cyclodehydrogenation is a versatile reaction that has enabled the syntheses of numerous polycyclic aromatic hydrocarbons (PAHs). We now describe a unique Scholl reaction of 6,7,13,14-tetraarylbenzo[k]tetraphene, which "unexpectedly" forms five-membered rings accompanying highly selective 1,2-shift of aryl groups. The geometric and optoelectronic nature of the resulting bistetracene analogue with five-membered rings is comprehensively investigated by single-crystal X-ray, NMR, UV-vis absorption, and cyclic voltammetry analyses. Furthermore, a possible mechanism is proposed to account for the selective five-membered-ring formation with the rearrangement of the aryl groups, which can be ration…
Fused Dibenzo[ a , m ]rubicene: A New Bowl-Shaped Subunit of C 70 Containing Two Pentagons
Total synthetic approaches of fullerenes are the holy grail for organic chemistry. So far, the main attempts have focused on the synthesis of the buckminsterfullerene C60. In contrast, access to subunits of the homologue C70 remains challenging. Here, we demonstrate an efficient bottom-up strategy toward a novel bowl-shaped polycyclic aromatic hydrocarbons (PAH) C34 with two pentagons. This PAH represents a subunit for C70 and of other higher fullerenes. The bowl-shaped structure was unambiguously determined by X-ray crystallography. A bowl-to-bowl inversion for a C70 fragment in solution was investigated by dynamic NMR analysis, showing a bowl-to-bowl inversion energy (ΔG(⧧)) of 16.7 kcal …
CCDC 1428696: Experimental Crystal Structure Determination
Related Article: Junzhi Liu, Akimitsu Narita, Silvio Osella, Wen Zhang, Dieter Schollmeyer, David Beljonne, Xinliang Feng, and Klaus Müllen|2016|J.Am.Chem.Soc.|138|2602|doi:10.1021/jacs.5b10399
CCDC 1472204: Experimental Crystal Structure Determination
Related Article: Junzhi Liu, Silvio Osella, Ji Ma, Reinhard Berger, David Beljonne, Dieter Schollmeyer, Xinliang Feng, and Klaus Müllen|2016|J.Am.Chem.Soc.|138|8364|doi:10.1021/jacs.6b04426
CCDC 1428694: Experimental Crystal Structure Determination
Related Article: Junzhi Liu, Akimitsu Narita, Silvio Osella, Wen Zhang, Dieter Schollmeyer, David Beljonne, Xinliang Feng, and Klaus Müllen|2016|J.Am.Chem.Soc.|138|2602|doi:10.1021/jacs.5b10399
CCDC 1427947: Experimental Crystal Structure Determination
Related Article: Junzhi Liu, Akimitsu Narita, Silvio Osella, Wen Zhang, Dieter Schollmeyer, David Beljonne, Xinliang Feng, and Klaus Müllen|2016|J.Am.Chem.Soc.|138|2602|doi:10.1021/jacs.5b10399
CCDC 1428695: Experimental Crystal Structure Determination
Related Article: Junzhi Liu, Akimitsu Narita, Silvio Osella, Wen Zhang, Dieter Schollmeyer, David Beljonne, Xinliang Feng, and Klaus Müllen|2016|J.Am.Chem.Soc.|138|2602|doi:10.1021/jacs.5b10399
CCDC 1472205: Experimental Crystal Structure Determination
Related Article: Junzhi Liu, Silvio Osella, Ji Ma, Reinhard Berger, David Beljonne, Dieter Schollmeyer, Xinliang Feng, and Klaus Müllen|2016|J.Am.Chem.Soc.|138|8364|doi:10.1021/jacs.6b04426