Download PDF
Synfacts 2024; 20(09): 0917
DOI: 10.1055/s-0043-1775276
Synthesis of Materials and Unnatural Products

Enantioselective Syntheses of π-Extended Carbohelicenes

Contributor(s):
Dahui Zhao
,
Xiao Xiao
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
CrossrefSearch in Google Scholar
› Further Information
 
 PDF Download Permissions and Reprints

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.


#

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.


#
#

Publication History

Article published online:
16 August 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany


  Permissions and Reprints