Repository logo

Infoscience

  • English
  • French
Log In
Logo EPFL, École polytechnique fédérale de Lausanne

Infoscience

  • English
  • French
Log In
  1. Home
  2. Academic and Research Output
  3. Journal articles
  4. Inherently chiral nor-heteracalixarenes: design and synthesis via enantioselective intramolecular Suzuki-Miyaura reaction
 
journal article

Inherently chiral nor-heteracalixarenes: design and synthesis via enantioselective intramolecular Suzuki-Miyaura reaction

Jiang, Yi-Fan
•
Tong, Shuo  
•
Zhu, Jieping  
Show more
July 3, 2024
Chemical Science

There has been a recent upsurge in research aimed at synthesizing inherently chiral molecules devoid of point, axial, planar and helical chiralities. We present herein our design and enantioselective synthesis of a series of inherently chiral macrocycles. These compounds, termed nor-heteracalixaromatics, feature a biaryl bond that replaces one of the aryl-heteroatom-aryl linkages found in classic heteracalix[4] aromatics. Macrocyclization of linear achiral substrates via an intramolecular Suzuki-Miyaura crosscoupling reaction affords the 15-membered cyclophane without any chiral elements in high yields and enantioselectivities. Notably, the formation of the aryl-aryl bond does not induce axial chirality at the biaryl linkage. Instead, it restricts the free rotation of an aromatic ring located four bonds away, leading to the inherent chirality of the macrocycle. The intriguing chiroptical properties of these compounds made them promising platform for the development of CPL emitters.

  • Files
  • Details
  • Metrics
Type
journal article
DOI
10.1039/d4sc03506b
Author(s)
Jiang, Yi-Fan
Tong, Shuo  
Zhu, Jieping  

EPFL

Wang, Mei-Xiang
Date Issued

2024-07-03

Publisher

Royal Society of Chemistry (RSC)

Published in
Chemical Science
Volume

15

Issue

31

Start page

12517

End page

12522

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSPN  
FunderFunding(s)Grant NumberGrant URL

National Natural Science Foundation of China

21920102001

École Polytechnique Fédérale de Lausanne

National Natural Science Foundation of China

22171160

Show more
Available on Infoscience
August 23, 2024
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/240831
Logo EPFL, École polytechnique fédérale de Lausanne
  • Contact
  • infoscience@epfl.ch

  • Follow us on Facebook
  • Follow us on Instagram
  • Follow us on LinkedIn
  • Follow us on X
  • Follow us on Youtube
AccessibilityLegal noticePrivacy policyCookie settingsEnd User AgreementGet helpFeedback

Infoscience is a service managed and provided by the Library and IT Services of EPFL. © EPFL, tous droits réservés