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Unprecedented J‐Aggregated Dyes in Pure Organic Solvents
Author(s) -
Manzano Hegoi,
Esnal Ixone,
MarquésMatesanz Tamara,
Bañuelos Jorge,
LópezArbeloa Iñigo,
Ortiz María J.,
Cerdán Luis,
Costela Angel,
GarcíaMoreno Inmaculada,
Chiara Jose Luis
Publication year - 2016
Publication title -
advanced functional materials
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 6.069
H-Index - 322
eISSN - 1616-3028
pISSN - 1616-301X
DOI - 10.1002/adfm.201505051
Subject(s) - chromophore , substituent , materials science , solvent , bodipy , photochemistry , aryl , molecular dynamics , organic chemistry , computational chemistry , chemistry , fluorescence , physics , alkyl , quantum mechanics
The design and synthesis of the first organic dyes enabling spontaneous formation of stable J‐aggregates in common organic solvents without additives is described. 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 B ‐spiranic 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 boradiazaindacene. 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.