Unprecedented J-Aggregated Dyes in Pure Organic Solvents
| Autor: | Jose Luis Chiara, Angel Costela, Hegoi Manzano, Ixone Esnal, Tamara Marqués-Matesanz, Iñigo López-Arbeloa, Luis Cerdán, Inmaculada García-Moreno, Jorge Bañuelos, Maria J. Ortiz |
|---|---|
| Přispěvatelé: | Ministerio de Economía y Competitividad (España), Eusko Jaurlaritza |
| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
fluorescent dyes
BODIPY dyes 010405 organic chemistry Chemistry Substituent Alkylation Chromophore 010402 general chemistry Condensed Matter Physics Boradiazaindacene 01 natural sciences J-aggregates 0104 chemical sciences Electronic Optical and Magnetic Materials Biomaterials Solvent chemistry.chemical_compound Computational chemistry Electrochemistry Organic chemistry BODIPY J-aggregate lasers Atomistic simulations |
| Zdroj: | Digital.CSIC. Repositorio Institucional del CSIC instname |
| Popis: | We describe the design and synthesis of the first organic dyes enabling spontaneous formation of stable J-aggregates in common organic solvents without additives. The new dyes are O-BODIPYs with a B-spiranic 4,4-diacyloxyl substitution pattern. Key to the effectiveness of the J-aggregation process is the high conformational rigidity of the Bspiranic molecular design as well as the orthogonal disposition of the B-diacyloxyl substituent and the meso-aryl group with respect to the mean plane of the borodiazaindacene. Atomistic simulations, both in vacuum and in a solvent cage, support the dynamics of the J-aggregation process as well as its dependence on the alkylation pattern of the BODIPY chromophore. A detailed analysis of the photophysical and laser properties of the new dyes provides convincing evidence for the unambiguous assignment of these J-aggregates and their dependence on the environmental conditions. We gratefully acknowledge financial support by the Spanish Ministerio de Economia y Competitividad (projects MAT2014-51937-C3-1-P, MAT2014- 51937-C3-2-P, MAT2014-51937-C3-3-P, and MAT2015-68837-REDT). I. E. thanks the Gobierno Vasco (IT339-10) for a predoctoral contract. H. M. acknowledges the Spanish Ministerio de Economia y Competitividad for a Juan de la Cierva postdoctoral contract. The authors thank SGIker of UPV/EHU for technical and human support with the X-ray diffraction measurements and computational calculations, which were carried out in the “arina” informatic cluster. We also thank Diego Plaza Lozano for preliminary synthetic studies. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|