Fluorescent molecular systems based on carborane-perylenediimide conjugates
This study presents the successful synthesis of two perylenediimide (PDI)-based ortho-carborane (o-carborane) derivatives, PDI-CB1 and PDI-CB2, through the insertion of decaborane into alkyne-terminated PDIs (PDI1 and PDI2). The introduction of o-carborane groups did not alter the optical properties...
| Autores: | , , , , |
|---|---|
| Formato: | artículo |
| Fecha de publicación: | 2024 |
| País: | España |
| Recursos: | Universitat Autònoma de Barcelona |
| Repositorio: | Dipòsit Digital de Documents de la UAB |
| Idioma: | inglés |
| OAI Identifier: | oai:ddd.uab.cat:309090 |
| Acesso em linha: | https://ddd.uab.cat/record/309090 https://dx.doi.org/urn:doi:10.1039/d4dt02477j |
| Access Level: | acceso abierto |
| Resumo: | This study presents the successful synthesis of two perylenediimide (PDI)-based ortho-carborane (o-carborane) derivatives, PDI-CB1 and PDI-CB2, through the insertion of decaborane into alkyne-terminated PDIs (PDI1 and PDI2). The introduction of o-carborane groups did not alter the optical properties of the PDI units in solution compared to their carborane-free counterparts, maintaining excellent fluorescence quantum yields of around 100% in various solvents. This was achieved by using a methylene linker to minimize electronic interaction between PDI and o-carborane, and by incorporating bulky o-carborane groups at imide- position to enhance solubility and prevent π-π stacking-induced aggregation. Aggregation studies demonstrated that PDI-CB1 and PDI-CB2 have greater solubility than PDI1 and PDI2 in both nonpolar and aqueous solvents. Despite the steric hindrance imparted by the o-carborane units, the solid state emission of PDI-CB1 and PDI-CB2 was affected by aggregation-caused fluorescence quenching. However, solid PDI-CB1 preserved bright red excimer-type emission, which persisted in water-dispersible nanoparticles, indicating potential for application as a theranostic agent combining fluorescence bioimaging with anticancer boron neutron capture therapy (BNCT) due to its high boron content. |
|---|