Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 61, Pages 13990-14001Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202002920
Keywords
fluorescence; phenylstyrylarenes; pi interactions; short-range exciton coupling; solid-state luminescence enhancements
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Funding
- Ministerio de Economia y Competitividad/Agencia Estatal de Investigacion/FEDER (Spain) [CTQ2017-84561-P]
- Universidad de Castilla-La Mancha [GI20163441, GI20173955, 2019-GRIN-27152]
- Consejeria de Economia y Conocimiento Junta de Andalucia [FQM-337]
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Different molecular strategies have been carefully evaluated to produce solid-state luminescence enhancement (SLE) in compounds that show dark states in solution. A set of alpha-phenylstyrylarene derivatives with a butterfly shape have been designed and synthesised, for the first time, with the aim of improving the solid-state fluorescence emission of their parent styrylarene compounds. Although these butterfly molecules are not fluorescent in solution, one of them (1,2,4,5-tetra(alpha-phenylstyryl)benzene) exhibits a fluorescence quantum yield as high as 68 % in a drop-cast sample and 31 % in its crystalline form. In contrast, 1,3,5-tris(alpha-phenylstyryl)benzene and 4,6-bis(alpha-phenylstyryl)pyrimidine do not show SLE. A range of fluorescence spectroscopy experiments and DFT calculations were carried out to unravel the origin of different photophysical behaviour of these compounds in the solid state. The results indicate that a rational strategy to control the SLE effect in luminogens depends on a delicate balance between molecular properties and inter-/intramolecular interactions in the solid state.
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