Homochiral Self‐Sorting During Macrocycle Formation and their Chiroptical Properties
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...
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2025-06-01
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| Series: | ChemistryOpen |
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| Online Access: | https://doi.org/10.1002/open.202400400 |
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| author | Diptiprava Sahoo Dr. Soumen De |
| author_facet | Diptiprava Sahoo Dr. Soumen De |
| author_sort | Diptiprava Sahoo |
| collection | DOAJ |
| description | 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 1H 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. |
| format | Article |
| id | doaj-art-32760601dc3c413c8cf2b8347b37edd7 |
| institution | Kabale University |
| issn | 2191-1363 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | ChemistryOpen |
| spelling | doaj-art-32760601dc3c413c8cf2b8347b37edd72025-08-20T03:24:43ZengWiley-VCHChemistryOpen2191-13632025-06-01146n/an/a10.1002/open.202400400Homochiral Self‐Sorting During Macrocycle Formation and their Chiroptical PropertiesDiptiprava Sahoo0Dr. Soumen De1School of Chemistry Indian Institute of Science Education and Research Thiruvananthapuram (IISER-TVM) 695551 Thiruvananthapuram IndiaSchool of Chemistry Indian Institute of Science Education and Research Thiruvananthapuram (IISER-TVM) 695551 Thiruvananthapuram IndiaAbstract 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 1H 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.https://doi.org/10.1002/open.202400400ChiralitySelf-SortingMacrocycleImine bondChiroptical properties |
| spellingShingle | Diptiprava Sahoo Dr. Soumen De Homochiral Self‐Sorting During Macrocycle Formation and their Chiroptical Properties ChemistryOpen Chirality Self-Sorting Macrocycle Imine bond Chiroptical properties |
| title | Homochiral Self‐Sorting During Macrocycle Formation and their Chiroptical Properties |
| title_full | Homochiral Self‐Sorting During Macrocycle Formation and their Chiroptical Properties |
| title_fullStr | Homochiral Self‐Sorting During Macrocycle Formation and their Chiroptical Properties |
| title_full_unstemmed | Homochiral Self‐Sorting During Macrocycle Formation and their Chiroptical Properties |
| title_short | Homochiral Self‐Sorting During Macrocycle Formation and their Chiroptical Properties |
| title_sort | homochiral self sorting during macrocycle formation and their chiroptical properties |
| topic | Chirality Self-Sorting Macrocycle Imine bond Chiroptical properties |
| url | https://doi.org/10.1002/open.202400400 |
| work_keys_str_mv | AT diptipravasahoo homochiralselfsortingduringmacrocycleformationandtheirchiropticalproperties AT drsoumende homochiralselfsortingduringmacrocycleformationandtheirchiropticalproperties |