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Synfacts 2012; 8(6): 0612
DOI: 10.1055/s-0031-1291058
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Helically Chiral 1,1′-Bitriphenylenes

Contributor(s):
Timothy M. Swager
,
Eilaf Ahmed
Sawada Y, Furumi S, Takai A, Takeuchi M, Noguchi K, Tanaka K * Tokyo University of Agriculture and Technology, National Institute for Materials Science, Tsukuba and Science and Technology Agency, Kawaguchi, Japan
Rhodium-Catalyzed Enantioselective Synthesis, Crystal Structures, and Photophysical Properties of Helically Chiral 1,1′-Bitriphenylenes.

J. Am. Chem. Soc. 2012;
134: 4080-4083
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Publication History

Publication Date:
16 May 2012 (online)

 
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Key words

rhodium-catalyzed [2+2+2] cycloaddition - chiral bitriphenylenes - [7]helicenes - fluorenes

Significance

The unique helical chirality of helicenes makes them attractive candidates for optical and electronic applications. This paper reports the synthesis of [7]helicenes, helically chiral 1,1′-bitriphenylenes, via rhodium-catalyzed double [2+2+2] cycloaddition. The scope of this method was examined by varying the R1 and R2 groups, ranging from electron-deficient to electron-rich groups, to give the corresponding helicenes in good yields (60–73%) and 60–93% ee.


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Comment

The authors report a highly enantioselective method of making [7]helicenes containing fluorene, spirofluorene and phosphafluorene. Circularly polarized luminescence properties of these helicenes containing fluorene and spirofluorene are significantly larger than those of known helicene derivatives.


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