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Synfacts 2023; 19(05): 0451
DOI: 10.1055/s-0042-1751875
Synthesis of Materials and Unnatural Products

Expanded [23]-Helicene

Contributor(s):
Dahui Zhao
,
Pai Wang
Kiel GR, Bergman HM, Samkian AE, Schuster NJ, Handford RC, Rothenberger AJ, Gomez-Bombarelli R, Nuckolls C, Tilley TD. * University of California, Berkeley, USA
Expanded [23]-Helicene with Exceptional Chiroptical Properties via an Iterative Ring-Fusion Strategy.

J. Am. Chem. Soc. 2022;
144: 23421-23427
DOI: 10.1021/jacs.2c09555.
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Key words

helicenes - linear/angular ring fusion - chiroptical properties - [2+2+2] reaction

Significance

Large helical structures are unique and sometimes irreplaceable molecular scaffolds serving special functions. By combining linear and angular ring-fusion modules, a set of expanded helicenes are designed and synthesized via convenient procedures, demonstrating extraordinary chiroptical properties reaching into the visible range.


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Comment

The key step to attaining the large helicenes­ first requires the assembly of polyaryl precursors comprising one or more 2,2′-diethynylbiphenyl moieties. Then, iridium- or rhodium-catalyzed [2+2+2] reactions are performed to accomplish helicenes composed of 15, 19, and 23 rings in the circuit.


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Publication History

Article published online:
14 April 2023

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