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Synfacts 2024; 20(09): 0917
DOI: 10.1055/s-0043-1775276
DOI: 10.1055/s-0043-1775276
Synthesis of Materials and Unnatural Products
Enantioselective Syntheses of π-Extended Carbohelicenes
Morita F,
Kishida Y,
Sato Y,
Sugiyama H,
Abekura M,
Nogami J,
Toriumi N,
Nagashima Y,
Kinoshita T,
Fukuhara G,
Uchiyama M,
Uekusa H,
Tanaka K.
*
Tokyo Institute of Technology, Japan
Design and Enantioselective Synthesis of 3D π-Extended Carbohelicenes for Circularly Polarized Luminescence.
Nat. Synth. 2024;
3: 774-786
DOI: 10.1038/s44160-024-00527-3.
Design and Enantioselective Synthesis of 3D π-Extended Carbohelicenes for Circularly Polarized Luminescence.
Nat. Synth. 2024;
3: 774-786
DOI: 10.1038/s44160-024-00527-3.
Key words
circularly polarized luminescence - carbohelicenes - [2+2+2] cycloaddition - Scholl reaction
Significance
π-Extended helicenes of intrinsic chirality are promising circularly polarized luminescence (CPL) emitters, but their preparations and resolution are challenging. Here, enantioselective syntheses of 3D π-extended carbo[11] and carbo[13] helicenes with bright CPL emissions and large asymmetry coefficients are achieved.
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Comment
The synthesis features enantioselective triple [2+2+2] cycloaddition, followed by multi-fold annulation through Scholl reaction, which further reduces the helicene diameter. Crystallization of the enantioenriched helicene products readily yields nearly pure enantiomers.
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Publication History
Article published online:
16 August 2024
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