Homochiral Self‐Sorting During Macrocycle Formation and their Chiroptical Properties

Diptiprava Sahoo; Soumen De

doi:10.1002/open.202400400

journal article Open Access Nov 26, 2024

Homochiral Self‐Sorting During Macrocycle Formation and their Chiroptical Properties

Diptiprava Sahoo

Soumen De

ChemistryOpen Vol. 14 No. 6 · Wiley

View at Publisher Save 10.1002/open.202400400

Abstract

Abstract

Several BINOL‐derived C2‐symmetric aldehydes were synthesized to investigate chiral self‐sorting phenomena during macrocycle formation in the presence of aliphatic and aromatic bisamines. While self‐sorting was unsuccessful with aliphatic amines, aromatic amine dictated complete homochiral self‐sorting, confirmed by
1
H NMR analysis and molecular modelling. Additionally, the impact of macrocyclization on the chiroptical properties of these macrocycles was examined. The Cotton effects band red‐shifted for aromatic amines owing to extended conjugation. Notably, a substantial increase in specific rotation was observed upon macrocycle formation.

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Details

Published: Nov 26, 2024
Vol/Issue: 14(6)
License: View

Authors

D

Diptiprava Sahoo

School of Chemistry Indian Institute of Science Education and Research Thiruvananthapuram (IISER-TVM) 695551 Thiruvananthapuram India

S

Soumen De

School of Chemistry Indian Institute of Science Education and Research Thiruvananthapuram (IISER-TVM) 695551 Thiruvananthapuram India

Funding

Indian Institute of Science Education and Research Thiruvananthapuram

Cite This Article

Diptiprava Sahoo, Soumen De (2024). Homochiral Self‐Sorting During Macrocycle Formation and their Chiroptical Properties. ChemistryOpen, 14(6). https://doi.org/10.1002/open.202400400

Homochiral Self‐Sorting During Macrocycle Formation and their Chiroptical Properties

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