Hexa-peri-hexabenzocoronenes by efficient oxidative cyclodehydrogenation: the role of the oligophenylene precursors

Hexa-peri-hexabenzocoronenes by efficient oxidative cyclodehydrogenation: the role of the oligophenylene precursors

[reaction: see text] Oligophenylene precursors based on 1,3,5-tris-(2'-biphenyl)ylbenzene (4a) and 1,4-bis-(2'-biphenyl)yl-2,5-diphenylbenzene (5a) were prepared and utilized for efficient hexabenzocoronene (HBC) synthesis by cyclodehydrogenations. Parent HBC 6a was efficiently synthesized...

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Veröffentlicht in:Organic letters 2006-03, Vol.8 (6), p.1145-1148
Hauptverfasser: Feng, Xinliang, Wu, Jishan, Enkelmann, Volk, Müllen, Klaus
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container_end_page 1148
container_issue 6
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container_title Organic letters
container_volume 8
creator Feng, Xinliang
Wu, Jishan
Enkelmann, Volk
Müllen, Klaus
description [reaction: see text] Oligophenylene precursors based on 1,3,5-tris-(2'-biphenyl)ylbenzene (4a) and 1,4-bis-(2'-biphenyl)yl-2,5-diphenylbenzene (5a) were prepared and utilized for efficient hexabenzocoronene (HBC) synthesis by cyclodehydrogenations. Parent HBC 6a was efficiently synthesized from the 1,3,5-tris-(2'-biphenyl)ylbenzene precursor, and novel D(3)(h)() symmetrical HBCs were prepared from 1,3,5-tris-(2'-biphenyl)ylbenzenes with various substitution types. For the preparation of a tert-butyl containing HBC 7 with D(2)(h)() symmetry, a two-step cyclodehydrogenation was required because of changes in the spin density distribution.
doi_str_mv 10.1021/ol053043z
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title Hexa-peri-hexabenzocoronenes by efficient oxidative cyclodehydrogenation: the role of the oligophenylene precursors
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