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Molecules 2013, 18(11), 13680-13690; doi:10.3390/molecules181113680
Article

Synthesis and Properties of Annulated 2-(Azaar-2-yl)- and 2,2'-Di(azaar-2-yl)-9,9'-spirobifluorenes

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Received: 5 August 2013; in revised form: 29 October 2013 / Accepted: 30 October 2013 / Published: 5 November 2013
(This article belongs to the Section Organic Synthesis)
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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.
Keywords: 9,9'-spirobifluorene; quinoline; 1,8-naphthyridine; benzo[h]quinoline; 1,10-phenanthroline; XRD; photoluminescence 9,9'-spirobifluorene; quinoline; 1,8-naphthyridine; benzo[h]quinoline; 1,10-phenanthroline; XRD; photoluminescence
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Liang, J.L.; Cha, H.; Jahng, Y. Synthesis and Properties of Annulated 2-(Azaar-2-yl)- and 2,2'-Di(azaar-2-yl)-9,9'-spirobifluorenes. Molecules 2013, 18, 13680-13690.

AMA Style

Liang JL, Cha H, Jahng Y. Synthesis and Properties of Annulated 2-(Azaar-2-yl)- and 2,2'-Di(azaar-2-yl)-9,9'-spirobifluorenes. Molecules. 2013; 18(11):13680-13690.

Chicago/Turabian Style

Liang, Jing L.; Cha, Hyochang; Jahng, Yurngdong. 2013. "Synthesis and Properties of Annulated 2-(Azaar-2-yl)- and 2,2'-Di(azaar-2-yl)-9,9'-spirobifluorenes." Molecules 18, no. 11: 13680-13690.


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