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Boron in disguise: the parent "fused" BN indole.

ABSTRACT: "Fused" BN indoles are an emerging class of boron-containing indole mimics, featuring geometric structure and electophilic aromatic substitution reactivity similar to those of indoles but exhibiting distinct electronic structure, leading to unique optoelectronic properties. Herein we report the synthesis of the parent N-H BN indole and provide a head-to-head comparison of the structural features, pK(a) values, and optoelectronic properties of this hybrid organic/inorganic indole with the classic natural indole.

SUBMITTER: Abbey ER

PROVIDER: S-EPMC3150194 | biostudies-other | 2011 Aug

REPOSITORIES: biostudies-other

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Boron in disguise: the parent "fused" BN indole.

Abbey Eric R ER Zakharov Lev N LN Liu Shih-Yuan SY

Journal of the American Chemical Society 20110713 30

"Fused" BN indoles are an emerging class of boron-containing indole mimics, featuring geometric structure and electophilic aromatic substitution reactivity similar to those of indoles but exhibiting distinct electronic structure, leading to unique optoelectronic properties. Herein we report the synthesis of the parent N-H BN indole and provide a head-to-head comparison of the structural features, pK(a) values, and optoelectronic properties of this hybrid organic/inorganic indole with the classic ...[more]

PMID: 21751771

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