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Synthesis and properties of annulated 2-(Azaar-2-yl)- and 2,2'-Di(azaar-2-yl)-9,9'-spirobifluorenes.

ABSTRACT: A series of 9,9'-spirobifluorene-derived N-heterocycles were prepared by the reactions of 8,9-dihydrospiro(benzo[b]fluorene-11,9'-fluoren)-6(7H)-one and 8,8',9,9'-tetrahydro-11,11'-spirobi(benzo[b]fluorene)-6,6'(7H,7'H)-dione with a series of 2-amino-arenecarbaldehydes such as 2-aminobenzaldehyde, 2-aminonicotinealdehyde, 1-amino-2-naphthaldehyde, and 8-aminoquinoline-7-carbaldehyde. In addition to the absorption maxima based on the parent 9,9'-spirobifluorene skeleton in the 225-234, 239-280, 296-298, and 308-328 nm regions, the absorptions due to the π-π* transitions of the heterocycles were observed in the 351-375 nm region in the UV absorption spectra. All the compounds showed strong photoluminescences in the 390-430 nm region.

SUBMITTER: Liang JL

PROVIDER: S-EPMC6270136 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

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Synthesis and properties of annulated 2-(Azaar-2-yl)- and 2,2'-Di(azaar-2-yl)-9,9'-spirobifluorenes.

Liang Jing Lu JL Cha Hyochang H Jahng Yurngdong Y

Molecules (Basel, Switzerland) 20131105 11

A series of 9,9'-spirobifluorene-derived N-heterocycles were prepared by the reactions of 8,9-dihydrospiro(benzo[b]fluorene-11,9'-fluoren)-6(7H)-one and 8,8',9,9'-tetrahydro-11,11'-spirobi(benzo[b]fluorene)-6,6'(7H,7'H)-dione with a series of 2-amino-arenecarbaldehydes such as 2-aminobenzaldehyde, 2-aminonicotinealdehyde, 1-amino-2-naphthaldehyde, and 8-aminoquinoline-7-carbaldehyde. In addition to the absorption maxima based on the parent 9,9'-spirobifluorene skeleton in the 225-234, 239-280, 2 ...[more]

PMID: 24196414

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