Synthesis and luminescence properties of analogues of the green fluorescent protein chromophore

Esteves, Cátia I. C.; Fonseca, Inês da Silva; Rocha, João; Silva, Artur M. S.; Guieu, Samuel

doi:10.1016/j.dyepig.2020.108267

Cited by 7 publications

(8 citation statements)

References 35 publications

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“…In solution, the synthesized chromophores present weak emission, due to the relaxation through the Z/E isomerization and torsional vibration of the aromatic rings. This isomerization could be blocked in the aggregate or crystalline state, from where the emission was increased, as expected, and only the presence of the Z isomer was confirmed through the crystal structures [15]. The crystal packing of a chromophore is considered an important factor to achieve an enhanced emission.…”

Section: Crystallization and Aggregation-induced Emission Enhancement...supporting

confidence: 52%

“…A family of GFPc analogues has been synthesized using Erlenmeyer azlactone synthesis, followed by a reaction of the obtained oxazolones with p-anisidine to give origin to the benzamides ring opening with a final cyclization (chromophores 1a-c, Figure 2) [15]. The strategy is based on the introduction of rotational aromatic groups around the imidazolidinone core to increase the AIEE phenomena.…”

Section: Crystallization and Aggregation-induced Emission Enhancement...mentioning

confidence: 99%

“…Concerning the synthesis of GFPc analogues, two main strategies have been extensively used: the Erlenmeyer azlactone synthesis and a Knoevenagel condensation. Erlenmeyer-Plöchl azlactone synthesis consists in the condensation of aromatic aldehydes with hippuric acid in acetic anhydride to produce an azlactone [14], then a subsequent reaction with a primary amine leads to the GFPc analogue (Scheme 1) [15]. Concerning the Knoevenagel condensation applied to the synthesis of GFPc analogues, it involves the formation of the imidazolidine core, followed by a Knoevenagel condensation (Scheme 2) [9].…”

Section: Introductionmentioning

confidence: 99%

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Locking the GFP Fluorophore to Enhance Its Emission Intensity

et al. 2022

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The Green Fluorescent Protein (GFP) and its analogues have been widely used as fluorescent biomarkers in cell biology. Yet, the chromophore responsible for the fluorescence of the GFP is not emissive when isolated in solution, outside the protein environment. The most accepted explanation is that the quenching of the fluorescence results from the rotation of the aryl–alkene bond and from the Z/E isomerization. Over the years, many efforts have been performed to block these torsional rotations, mimicking the environment inside the protein β-barrel, to restore the emission intensity. Molecule rigidification through chemical modifications or complexation, or through crystallization, is one of the strategies used. This review presents an overview of the strategies developed to achieve highly emissive GFP chromophore by hindering the torsional rotations.

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Section: Crystallization and Aggregation-induced Emission Enhancement...supporting

confidence: 52%

Section: Crystallization and Aggregation-induced Emission Enhancement...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Locking the GFP Fluorophore to Enhance Its Emission Intensity

et al. 2022

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“…Fluorophores 1 ad and 1 bd present the lowest fluorescence quantum yield, probably due to the quenching effect of the nitro group. [19] Comparing 1 aa, 1 ba and 1 ca, the latter has the highest fluorescence quantum yield, due to the strong electron-donating dimethylamino substituent inducing a more pronounced push-pull character.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Influence of the Intramolecular Hydrogen Bond on the Fluorescence of 2‐ortho‐Aminophenyl Pyridines

Esteves

Fontes

Rocha

et al. 2022

Chemistry A European J

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The dynamic nature of excited-state intramolecular proton transfer (ESIPT) and its effect on emission spectra is an attractive strategy to create multi-emissive dyes. Here we describe the behavior of a series of hydrogen-bonded triphenylpyridines with a set of donor-acceptor combinations that allowed us to perceive the influence of each substitution on the photophysical properties of the dyes. The susceptibility of these ESIPT moieties to pH variations was also studied, elucidating that the level of protonation had a significant effect on the emission color. The assignment of each emission band was made by using DFT and td-DFT calculations that were in agreement with the experimental results. This study emphasizes the versatility of triphenylpyridines that can be synthesized effortlessly with a logical and independent C-2, C-4 and C-6 substitution in order to have the desired ESIPT modulation and subsequent multi-emission response.

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“…[15] Heteroaromatic chromophores bearing twisted aromatic substituents have emerged as promising candidates for deep blue emission, [15,16] sometimes through thermally activated delayed fluorescence. [17] This goal is difficult to reach, because fluorophores bearing aromatic substituents which can rotate freely often present very small quantum yields in solution, due to non-radiative relaxation, and only emit when those rotations are restricted, for example in aggregate [4,13,18,19] or crystalline state, [5] or when they interact with macromolecules. [12] This general behavior is named aggregation-induced emission enhancement (AIEE), [20] and has been widely studied and applied to biological imaging [12,21,22] and luminescent devices.…”

Section: Introductionmentioning

confidence: 99%

Unsymmetrical 2,4,6‐Triarylpyridines as Versatile Scaffolds for Deep‐Blue and Dual‐Emission Fluorophores

Fontes

Silva

et al. 2020

ChemPhotoChem

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Pyridines substituted with different aromatic groups at C-2, C-4 and C-6 were prepared following a Kröhnke 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 deepblue and dual emission fluorophores, and are promising building blocks for luminescent devices and sensors.

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Synthesis and luminescence properties of analogues of the green fluorescent protein chromophore

Cited by 7 publications

References 35 publications

Locking the GFP Fluorophore to Enhance Its Emission Intensity

Locking the GFP Fluorophore to Enhance Its Emission Intensity

Influence of the Intramolecular Hydrogen Bond on the Fluorescence of 2‐ortho‐Aminophenyl Pyridines

Unsymmetrical 2,4,6‐Triarylpyridines as Versatile Scaffolds for Deep‐Blue and Dual‐Emission Fluorophores

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