Unsymmetrical 2,4,6-Triarylpyridines as Versatile Scaffolds for Deep-Blue and Dual-Emission Fluorophores
authors Fontes, LFB; da Silva, RN; Silva, AMS; Guieu, S
nationality International
journal CHEMPHOTOCHEM
author keywords triphenylpyridine; fluorescence; deep blue; dual emission; excited state intramolecular proton transfer
keywords AGGREGATION-INDUCED EMISSION; ACTIVATED DELAYED FLUORESCENCE; ENHANCEMENT; SYSTEMS; DESIGN
abstract Pyridines substituted with different aromatic groups at C-2, C-4 and C-6 were prepared following a Krohnke synthetic route. Introducing ortho-anisole at C-2 resulted in deep blue emitters in solution, with quantum yields up to 74%. On the other hand, when ortho-phenol was introduced, forming a strong hydrogen bond with the pyridine nitrogen, excited-state intramolecular proton transfer was witnessed by the dual emission of the fluorophores, which is sensitive to the dye environment. The phenyl ring at C-4 was used to introduce electron-donating or withdrawing groups, to fine-tune the photophysical properties of the dyes. Crystal structures of the fluorophores, together with theoretical studies using DFT/TD-DFT calculations, were used to rationalize the experimental photophysical properties of the two families of dyes. Unsymmetrical 2,4,6-triarylpyridines are therefore versatile scaffolds for the preparation of deep-blue and dual emission fluorophores, and are promising building blocks for luminescent devices and sensors.
publisher WILEY-V C H VERLAG GMBH
issn 2367-0932
year published 2020
digital object identifier (doi) 10.1002/cptc.202000134
web of science category Chemistry, Physical
subject category Chemistry
unique article identifier WOS:000548280000001
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journal analysis (jcr 2019):
journal impact factor 2.838
5 year journal impact factor 2.843
category normalized journal impact factor percentile 49.371
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