Kinetic Control of the Supramolecular Chirality of Porphyrin J-Aggregates
The aggregation of achiral sulfonatophenyl‐ and phenyl‐meso‐substituted diprotonated porphyrins to chiral J‐aggregates is a hierarchical noncovalent polymerization process preceded by a critical nucleation stage. This allows significant enantiomeric excesses by the formation of a few primary nuclei...
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| Published in | Chemistry : a European journal Vol. 18; no. 28; pp. 8820 - 8826 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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Weinheim
WILEY-VCH Verlag
09.07.2012
WILEY‐VCH Verlag Wiley Subscription Services, Inc |
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| Abstract | The aggregation of achiral sulfonatophenyl‐ and phenyl‐meso‐substituted diprotonated porphyrins to chiral J‐aggregates is a hierarchical noncovalent polymerization process preceded by a critical nucleation stage. This allows significant enantiomeric excesses by the formation of a few primary nuclei and the control of their growth by the effect that flows (imperfect mixing) have on the secondary nucleation of the J‐aggregate particles. In addition, the results strongly suggest that when only one species of aggregate predominates, the CD signals of the three excitonic bands in the visible region (around 420, 490, and 700 nm) show the same sign. Thus, differences on their relative sign would be due to the presence of different species.
How to avoid the racemic: The aggregation of achiral sulfonatophenyl‐ and phenyl‐meso‐substituted diprotonated porphyrins is a noncovalent polymerization process preceded by a critical nucleation stage that yields chiral J‐aggregates. Significant enantiomeric excesses are obtained by the formation of a few first nuclei and the control of their growth by the effect of flows (imperfect mixing) on the diffusion of clusters and J‐aggregate particles (see figure). |
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| AbstractList | The aggregation of achiral sulfonatophenyl- and phenyl-meso-substituted diprotonated porphyrins to chiral J-aggregates is a hierarchical noncovalent polymerization process preceded by a critical nucleation stage. This allows significant enantiomeric excesses by the formation of a few primary nuclei and the control of their growth by the effect that flows (imperfect mixing) have on the secondary nucleation of the J-aggregate particles. In addition, the results strongly suggest that when only one species of aggregate predominates, the CD signals of the three excitonic bands in the visible region (around 420, 490, and 700 nm) show the same sign. Thus, differences on their relative sign would be due to the presence of different species. The aggregation of achiral sulfonatophenyl- and phenyl-meso-substituted diprotonated porphyrins to chiral J-aggregates is a hierarchical noncovalent polymerization process preceded by a critical nucleation stage. This allows significant enantiomeric excesses by the formation of a few primary nuclei and the control of their growth by the effect that flows (imperfect mixing) have on the secondary nucleation of the J-aggregate particles. In addition, the results strongly suggest that when only one species of aggregate predominates, the CD signals of the three excitonic bands in the visible region (around 420, 490, and 700nm) show the same sign. Thus, differences on their relative sign would be due to the presence of different species. How to avoid the racemic: The aggregation of achiral sulfonatophenyl- and phenyl-meso-substituted diprotonated porphyrins is a noncovalent polymerization process preceded by a critical nucleation stage that yields chiral J-aggregates. Significant enantiomeric excesses are obtained by the formation of a few first nuclei and the control of their growth by the effect of flows (imperfect mixing) on the diffusion of clusters and J-aggregate particles (see figure). The aggregation of achiral sulfonatophenyl‐ and phenyl‐meso‐substituted diprotonated porphyrins to chiral J‐aggregates is a hierarchical noncovalent polymerization process preceded by a critical nucleation stage. This allows significant enantiomeric excesses by the formation of a few primary nuclei and the control of their growth by the effect that flows (imperfect mixing) have on the secondary nucleation of the J‐aggregate particles. In addition, the results strongly suggest that when only one species of aggregate predominates, the CD signals of the three excitonic bands in the visible region (around 420, 490, and 700 nm) show the same sign. Thus, differences on their relative sign would be due to the presence of different species. How to avoid the racemic: The aggregation of achiral sulfonatophenyl‐ and phenyl‐meso‐substituted diprotonated porphyrins is a noncovalent polymerization process preceded by a critical nucleation stage that yields chiral J‐aggregates. Significant enantiomeric excesses are obtained by the formation of a few first nuclei and the control of their growth by the effect of flows (imperfect mixing) on the diffusion of clusters and J‐aggregate particles (see figure). Abstract The aggregation of achiral sulfonatophenyl‐ and phenyl‐ meso ‐substituted diprotonated porphyrins to chiral J‐aggregates is a hierarchical noncovalent polymerization process preceded by a critical nucleation stage. This allows significant enantiomeric excesses by the formation of a few primary nuclei and the control of their growth by the effect that flows (imperfect mixing) have on the secondary nucleation of the J‐aggregate particles. In addition, the results strongly suggest that when only one species of aggregate predominates, the CD signals of the three excitonic bands in the visible region (around 420, 490, and 700 nm) show the same sign. Thus, differences on their relative sign would be due to the presence of different species. The aggregation of achiral sulfonatophenyl- and phenyl-meso-substituted diprotonated porphyrins to chiral J-aggregates is a hierarchical noncovalent polymerization process preceded by a critical nucleation stage. This allows significant enantiomeric excesses by the formation of a few primary nuclei and the control of their growth by the effect that flows (imperfect mixing) have on the secondary nucleation of the J-aggregate particles. In addition, the results strongly suggest that when only one species of aggregate predominates, the CD signals of the three excitonic bands in the visible region (around 420, 490, and 700nm) show the same sign. Thus, differences on their relative sign would be due to the presence of different species. |
| Author | Crusats, Joaquim Arteaga, Oriol Canillas, Adolf Ribo, Josep M. El-Hachemi, Zoubir Sorrenti, Alessandro |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/22678975$$D View this record in MEDLINE/PubMed |
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| Copyright | Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Snippet | The aggregation of achiral sulfonatophenyl‐ and phenyl‐meso‐substituted diprotonated porphyrins to chiral J‐aggregates is a hierarchical noncovalent... The aggregation of achiral sulfonatophenyl- and phenyl-meso-substituted diprotonated porphyrins to chiral J-aggregates is a hierarchical noncovalent... Abstract The aggregation of achiral sulfonatophenyl‐ and phenyl‐ meso ‐substituted diprotonated porphyrins to chiral J‐aggregates is a hierarchical noncovalent... |
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| SubjectTerms | Agglomeration Aggregates Bands Chemistry chirality circular dichroism Diffusion Formations Nucleation Nuclei Polymerization porphyrinoids Porphyrins self-assembly supramolecular chemistry |
| Title | Kinetic Control of the Supramolecular Chirality of Porphyrin J-Aggregates |
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