Globular Aggregates Stemming from the Self-Assembly of an Amphiphilic <i>N</i>-Annulated Perylene Bisimide in Aqueous Media
Herein, we describe the synthesis of highly emissive amphiphilic <i>N</i>-annulated PBI <b>1</b> decorated with oligo ethylene glycol (OEG) side chains. These polar side chains allow the straightforward solubility of <b>1</b> in solvents of different polarity such...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-05-01
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| Series: | Nanomaterials |
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| Online Access: | https://www.mdpi.com/2079-4991/11/6/1457 |
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| author | Manuel A. Martínez Elisa E. Greciano Jorge Cuéllar José M. Valpuesta Luis Sánchez |
| author_facet | Manuel A. Martínez Elisa E. Greciano Jorge Cuéllar José M. Valpuesta Luis Sánchez |
| author_sort | Manuel A. Martínez |
| collection | DOAJ |
| description | Herein, we describe the synthesis of highly emissive amphiphilic <i>N</i>-annulated PBI <b>1</b> decorated with oligo ethylene glycol (OEG) side chains. These polar side chains allow the straightforward solubility of <b>1</b> in solvents of different polarity such as water, iPrOH, dioxane, or chloroform. Compound <b>1</b> self-assembles in aqueous media by π-stacking of the aromatic units and van der Waals interactions, favored by the hydrophobic effect. The hypo- and hypsochromic effect observed in the UV-Vis spectra of <b>1</b> in water in comparison to chloroform is diagnostic of H-type aggregation. Solvent denaturation experiments allow deriving the free Gibbs energy for the self-assembly process in aqueous media and the factor <i>m</i> that is indicative of the influence exerted by a good solvent in the stability of the final aggregates. The ability of compound <b>1</b> to self-assemble in water yields globular aggregates that have been visualized by TEM imaging. |
| first_indexed | 2024-03-10T10:50:58Z |
| format | Article |
| id | doaj.art-9c29a2aed8d24621a76538fafac752b0 |
| institution | Directory Open Access Journal |
| issn | 2079-4991 |
| language | English |
| last_indexed | 2024-03-10T10:50:58Z |
| publishDate | 2021-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Nanomaterials |
| spelling | doaj.art-9c29a2aed8d24621a76538fafac752b02023-11-21T22:13:45ZengMDPI AGNanomaterials2079-49912021-05-01116145710.3390/nano11061457Globular Aggregates Stemming from the Self-Assembly of an Amphiphilic <i>N</i>-Annulated Perylene Bisimide in Aqueous MediaManuel A. Martínez0Elisa E. Greciano1Jorge Cuéllar2José M. Valpuesta3Luis Sánchez4Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040 Madrid, SpainDepartamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040 Madrid, SpainCentro Nacional de Biotecnología, Campus de la Universidad Autónoma de Madrid, 28049 Madrid, SpainCentro Nacional de Biotecnología, Campus de la Universidad Autónoma de Madrid, 28049 Madrid, SpainDepartamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040 Madrid, SpainHerein, we describe the synthesis of highly emissive amphiphilic <i>N</i>-annulated PBI <b>1</b> decorated with oligo ethylene glycol (OEG) side chains. These polar side chains allow the straightforward solubility of <b>1</b> in solvents of different polarity such as water, iPrOH, dioxane, or chloroform. Compound <b>1</b> self-assembles in aqueous media by π-stacking of the aromatic units and van der Waals interactions, favored by the hydrophobic effect. The hypo- and hypsochromic effect observed in the UV-Vis spectra of <b>1</b> in water in comparison to chloroform is diagnostic of H-type aggregation. Solvent denaturation experiments allow deriving the free Gibbs energy for the self-assembly process in aqueous media and the factor <i>m</i> that is indicative of the influence exerted by a good solvent in the stability of the final aggregates. The ability of compound <b>1</b> to self-assemble in water yields globular aggregates that have been visualized by TEM imaging.https://www.mdpi.com/2079-4991/11/6/1457amphiphileshydrophobic effectperylene bisimidesπ-stackingself-assembly |
| spellingShingle | Manuel A. Martínez Elisa E. Greciano Jorge Cuéllar José M. Valpuesta Luis Sánchez Globular Aggregates Stemming from the Self-Assembly of an Amphiphilic <i>N</i>-Annulated Perylene Bisimide in Aqueous Media Nanomaterials amphiphiles hydrophobic effect perylene bisimides π-stacking self-assembly |
| title | Globular Aggregates Stemming from the Self-Assembly of an Amphiphilic <i>N</i>-Annulated Perylene Bisimide in Aqueous Media |
| title_full | Globular Aggregates Stemming from the Self-Assembly of an Amphiphilic <i>N</i>-Annulated Perylene Bisimide in Aqueous Media |
| title_fullStr | Globular Aggregates Stemming from the Self-Assembly of an Amphiphilic <i>N</i>-Annulated Perylene Bisimide in Aqueous Media |
| title_full_unstemmed | Globular Aggregates Stemming from the Self-Assembly of an Amphiphilic <i>N</i>-Annulated Perylene Bisimide in Aqueous Media |
| title_short | Globular Aggregates Stemming from the Self-Assembly of an Amphiphilic <i>N</i>-Annulated Perylene Bisimide in Aqueous Media |
| title_sort | globular aggregates stemming from the self assembly of an amphiphilic i n i annulated perylene bisimide in aqueous media |
| topic | amphiphiles hydrophobic effect perylene bisimides π-stacking self-assembly |
| url | https://www.mdpi.com/2079-4991/11/6/1457 |
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