| Full text | |
| Author(s): |
Alcantara, Arthur F. P.
[1, 2]
;
Fontana, Liniquer A.
[1]
;
Almeida, Marlon P.
[1]
;
Rigolin, Vitor H.
[1]
;
Ribeiro, Marcos A.
[3]
;
Barros, Wdeson P.
[1]
;
Megiatto, Jr., Jackson D.
[1]
Total Authors: 7
|
| Affiliation: | [1] Univ Campinas UNICAMP, Inst Chem, POB 6154, BR-13083970 Campinas - Brazil
[2] Inst Fed Sertao Pernambucano, Estrada Tamboril, BR-56200000 Ouricuri - Brazil
[3] Univ Fed Espirito Santo, Dept Quim, Ave Fernando Ferrari 514, BR-29075910 Vitoria, ES - Brazil
Total Affiliations: 3
|
| Document type: | Journal article |
| Source: | CHEMISTRY-A EUROPEAN JOURNAL; v. 26, n. 35, p. 7808-7822, JUN 23 2020. |
| Web of Science Citations: | 4 |
| Abstract | |
A 5,15-bis(1,1 `-biphenyl)porphyrin-based molecular clip covalently connected to a ditopic aliphatic ester loop moiety yields a semi-rigid macrocycle with a well-defined cavity. The resulting macrocycle fits the structural requirements for the preparation of porphyrinates capable of promoting formation of C-C bonds. To demonstrate the usefulness of porphyrin-based macrocycles, an active-metal-template synthesis of rotaxanes through a redox non-innocent carbene transfer reaction is described. Coordination of Co-II ions into the porphyrin subunit followed by addition of appropriate monodentate nitrogen-based additives to function as axial ligands enables the radical carbene transfer reactions to styrene derivatives to occur exclusively through the cavity of the macrocycle to afford cyclopropane-linked rotaxanes in excellent 95 % yield. Investigation of the product distribution afforded from the rotaxane assembly reaction reveals how the redox cooperative action between the carbene species and the Co-II ions can be manipulated to gain control over the radical-type mechanism to favor the productive rotaxane forming process. (AU) | |
| FAPESP's process: | 17/06752-5 - Development of New Template Strategies for the Synthesis of Polyrotaxanes |
| Grantee: | Liniquer André Fontana |
| Support Opportunities: | Scholarships in Brazil - Doctorate |
| FAPESP's process: | 15/23761-2 - Development of new well-defined multifunctional dendrimers for applications in nanomedicine |
| Grantee: | Cátia Cristina Capêlo Ornelas Megiatto |
| Support Opportunities: | Regular Research Grants |
| FAPESP's process: | 13/22160-0 - Development of original synthetic strategies for the preparation of supramolecular Interlocked polymers |
| Grantee: | Jackson Dirceu Megiatto Junior |
| Support Opportunities: | Research Grants - Young Investigators Grants |