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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

,  and *
College of Pharmacy, Yeungnam University, Gyeongsan 712-749, Korea
* Author to whom correspondence should be addressed.
Received: 5 August 2013 / Revised: 29 October 2013 / Accepted: 30 October 2013 / Published: 5 November 2013
(This article belongs to the Section Molecular Diversity)
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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 (CC BY 3.0).

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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.

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