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Synfacts 2011(2): 0153-0153  
DOI: 10.1055/s-0030-1259247
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

(2,1-a)-Indenofluorene with Clapping Fluorenes

Contributor(s): Timothy M. Swager, Shuang Liu
D. Thirion, C. Poriel*, J. Rault-Berthelot, F. Barrière, O. Jeannin
Université de Rennes 1, France
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Publication History

Publication Date:
19 January 2011 (online)

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Significance

The authors report the improved synthesis of 11,12-dihydroindeno[2,1-a]fluorene ([2,1-a]-IF) and its dispirofluorene derivative [2,1-a]-DSF-IF. Several acid-promoted intramolecular cyclizations have been optimized to build the indenofluorene backbone, and the formation of [1,2-b]-isomers can be avoided. Both [2,1-a]-IF and [2,1-a]-DSF-IF show bright photoluminescence in solution (ΦF  ≈ 60%) and can be polymerized via anodic oxidation.