Diindeno[1,2,3,4-defg;1′,2′,3′,4′-mnop]chrysenes: Solution-phase synthesis and the bowl-to-bowl inversion barrier

Hung Ing Chang; Hsin Ting Huang; Cheng Hao Huang; Ming Yu Kuo; Yao Ting Wu

doi:10.1039/c0cc01730b

Diindeno[1,2,3,4-defg;1′,2′,3′,4′-mnop]chrysenes: Solution-phase synthesis and the bowl-to-bowl inversion barrier

Hung Ing Chang, Hsin Ting Huang, Cheng Hao Huang, Ming Yu Kuo, Yao Ting Wu

Department of Chemistry

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

29 Citations (Scopus)

Abstract

Diindeno[1,2,3,4-defg;1′,2′,3′,4′-mnop]chrysenes 2 were straightforwardly prepared in around 20% yield from 9,10- diarylphenanthrenes 3 by palladium-catalyzed intramolecular arylations. The bowl-to-bowl inversion barrier for buckybowl 2-iPr is predicted to be approximately 7 kcal mol^-1 based on density functional theory calculations and this value is consistent with the results of a variable-temperature ¹H-NMR study.

Original language	English
Pages (from-to)	7241-7243
Number of pages	3
Journal	Chemical Communications
Volume	46
Issue number	38
DOIs	https://doi.org/10.1039/c0cc01730b
Publication status	Published - 2010 Oct 14

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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abstract = "Diindeno[1,2,3,4-defg;1′,2′,3′,4′-mnop]chrysenes 2 were straightforwardly prepared in around 20% yield from 9,10- diarylphenanthrenes 3 by palladium-catalyzed intramolecular arylations. The bowl-to-bowl inversion barrier for buckybowl 2-iPr is predicted to be approximately 7 kcal mol-1 based on density functional theory calculations and this value is consistent with the results of a variable-temperature 1H-NMR study.",

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AU - Huang, Hsin Ting

AU - Huang, Cheng Hao

AU - Kuo, Ming Yu

AU - Wu, Yao Ting

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AB - Diindeno[1,2,3,4-defg;1′,2′,3′,4′-mnop]chrysenes 2 were straightforwardly prepared in around 20% yield from 9,10- diarylphenanthrenes 3 by palladium-catalyzed intramolecular arylations. The bowl-to-bowl inversion barrier for buckybowl 2-iPr is predicted to be approximately 7 kcal mol-1 based on density functional theory calculations and this value is consistent with the results of a variable-temperature 1H-NMR study.

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Diindeno[1,2,3,4-defg;1′,2′,3′,4′-mnop]chrysenes: Solution-phase synthesis and the bowl-to-bowl inversion barrier

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