Novel efficient fluorophores synthesized from citric acid

Kasprzyk, Wiktor; Bednarz, Szczepan; Żmudzki, Paweł; Galica, Mateusz; Bogdał, Dariusz

doi:10.1039/c5ra03226a

Cited by 119 publications

(104 citation statements)

References 51 publications

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“…The observed results are consistent with the mechanism of the formation of O-dots by combining fluorophores formed via the condensation of the molecules of citric acid and amines [38–40]. According to the suggested reaction mechanism, ethylenediamine and citric acid form a salt at elevated temperatures, before reacting to a large network, due to the multiple functional groups of both precursor molecules.…”

Section: Resultssupporting

confidence: 84%

Facile fabrication of luminescent organic dots by thermolysis of citric acid in urea melt, and their use for cell staining and polyelectrolyte microcapsule labelling

Nm¹,

Попов²,

Shcherbakov³

et al. 2016

Beilstein J. Nanotechnol.

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Luminescent organic dots (O-dots) were synthesized via a one-pot, solvent-free thermolysis of citric acid in urea melt. The influence of the ratio of the precursors and the duration of the process on the properties of the O-dots was established and a mechanism of their formation was hypothesized. The multicolour luminescence tunability and toxicity of synthesized O-dots were extensively studied. The possible applications of O-dots for alive/fixed cell staining and labelling of layer-by-layer polyelectrolyte microcapsules were evaluated.

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Section: Resultssupporting

confidence: 84%

Facile fabrication of luminescent organic dots by thermolysis of citric acid in urea melt, and their use for cell staining and polyelectrolyte microcapsule labelling

Nm¹,

Попов²,

Shcherbakov³

et al. 2016

Beilstein J. Nanotechnol.

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show abstract

“…[15] As illustrated in Scheme 1, in this study,t he supposed formation processes for the formation of the nonaromatic molecule involved five steps:a midation, [16] nucleophilic addition, dehydroxylation, cyclization reaction, and dehydroxylation, resulting in the nonaromatics tructure of 5-oxo-2,3-dihydro-5H-(1,3)thiazolo(3,2-a)pyridine-3,7-dicarboxylic acid (noted as TPA), as similar to the mechanism reported by Kasprzyka nd co-workers. [17] In their pioneering work, the solvento fw ater was removedf rom the CA + Cys aqueous mixtureu nder vacuum and then the mixture was heateda th igh temperature (180 8C), resulting in ac rude product that containsT PA. [18] Regardingt he reaction condition and preparation processes, no water evaporation and high temperatureo perations were required in our work;T PA was directly preparedb ys imple heating treatment of the aqueous mixtures of CA + Cys under mild conditions. This facile approach offerss everala dvantages as compared to previous reports, including easy operation, ecofriendly reactionroute, and alow cost and scalable production.…”

Section: Resultsmentioning

confidence: 99%

Facile Preparation of Bright‐Fluorescent Soft Materials from Small Organic Molecules

Wang

Yang

Liu

et al. 2016

Chemistry A European J

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Highly fluorescent and biocompatible soft materials are desirable for many potential applications, but their synthetic processes are somehow complicated. Herein, we have explored the feasibility of synthesis of unconventional fluorescence soft materials from small organic molecules under mild conditions. A new blue-fluorescent soft material with high quantum yield (89.6 %) and eutectic feature prepared by simple heat treatment of citric acid (CA) and cysteine (Cys) aqueous mixtures below 100 °C in air was reported. The as-prepared fluorescent material has the features of facile preparation, low cost, scalable production and easy to process, making it suitable for applications like fluorescent labeling and light-emitting devices. This new finding opens a new venue for the preparation of fluorescent soft materials.

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“…[35, 85] To examine this hypothesis, Kasprzyk et al reacted CA with five diﬀerent bifunctional amines, including cysteamine, L-cysteine, o -aminophenol, o -aminothiophenol and o -phenylenediamine, each at 180 °C for 1 h. [35] After being isolated with HPLC, their chemical structures were determined by 1 H, 13 C and HSQC NMR experiments, elemental analysis, high resolution and fragmentation spectra ESI-MS analyses. The results indicated these fluorescent compounds consist of five-membered ring fused 2-pyridones.…”

Section: Citrate-based Molecular Fluorophoresmentioning

confidence: 99%

Citrate‐Based Fluorescent Biomaterials

Shan

Hsieh

Bai

et al. 2018

Adv Healthcare Materials

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Fluorescence imaging has emerged as a promising technique for monitoring and assessing various biologically relevant species in cells and organisms, driving the demand for effective fluorescent agents with good biocompatibility and high fluorescence performance. However, traditional fluorescent agents, such as quantum dots (QDs) and organic dyes, either suffer from toxicity concerns or poor fluorescence performance (e.g., low photobleaching-resistance). In this regard, citrate-based fluorescent biomaterials, which are synthesized from the natural and biocompatible precursor of citric acid (CA), have become competitive alternatives for fluorescence imaging owing to their biocompatibility, cost effectiveness, straightforward synthetic routes, flexible designability, as well as strong fluorescence with adjustable excitation/emission wavelengths. Accordingly, numerous citrate-based biomaterials, including carbon dots (CDs), biodegradable photoluminescent polymers (BPLPs), and small molecular fluorophores, have been developed and researched in the past few decades. This review discusses recent progress in the research and development of citrate-based fluorescent materials with emphasis on their design and synthesis considerations, material properties, fluorescence properties and mechanisms, as well as biomedical applications. It is expected that this review will provide an insightful discussion on the citrate-based fluorescent biomaterials, and lead to innovations for the next generation of fluorescent biomaterials and fluorescence-based biomedical technology.

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Novel efficient fluorophores synthesized from citric acid

Abstract: Citric acid was reacted with α,β-diamines, β-amino thiols and β-amino alcohols to produce fluorescent derivatives of 2-pyridone (QY up to ∼79%). The chemical structures of these compounds were confirmed by analyses of 1D, 2D NMR and ESI-MS data.

Cited by 119 publications

References 51 publications

Facile fabrication of luminescent organic dots by thermolysis of citric acid in urea melt, and their use for cell staining and polyelectrolyte microcapsule labelling

Facile fabrication of luminescent organic dots by thermolysis of citric acid in urea melt, and their use for cell staining and polyelectrolyte microcapsule labelling

Facile Preparation of Bright‐Fluorescent Soft Materials from Small Organic Molecules

Citrate‐Based Fluorescent Biomaterials

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