Fluorescence enhancement of quinolines by protonation

Tervola, Essi; Truong, Khai‐Nghi; Ward, Jas S.; Priimägi, Arri

doi:10.1039/d0ra04691d

Cited by 30 publications

(23 citation statements)

References 44 publications

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“…In N‐substituted heteroacenes, the singlet state consists of a lower‐lying π‐π* state followed by a weak n‐π* state [49] . Depending on the various factors (solvent, position and number of N‐atoms) the energy gap between these levels may vary [50–53] . DFT calculations show that 5‐azatetracene has weak charge transfer properties while in tetracene there is no charge transfer.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 5‐Azatetracene and Comparison of Its Optical and Electrochemical Properties with Tetracene

Ghosh

Budanović

et al. 2021

Asian J Org Chem

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A four‐step route for the synthesis of 5‐azatetracene (benzo[b]acridine) has been developed, employing a base‐catalysed Friedlander condensation reaction between 3‐amino‐2‐napthaldehyde and cyclohexanone as the key step followed by dehydrogenation of the intermediate. The optical and electrochemical properties of the 5‐azatetracene were investigated by UV‐vis and photoluminescence spectroscopy, and by cyclic voltammetry and compared with those of tetracene. It is found that 5‐azatetracene shows broader absorption in the visible region than tetracene, exhibits a higher luminescence quantum efficiency, and possesses a lower‐lying LUMO level and smaller HOMO‐LUMO band gap. Time‐resolved PL spectroscopy was used to elucidate the reasons for the more efficient luminescence of 5‐azatetracene. Field‐effect transistor measurements revealed the ambipolar nature of charge transport in 5‐azatetracene.

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Section: Resultsmentioning

confidence: 99%

Synthesis of 5‐Azatetracene and Comparison of Its Optical and Electrochemical Properties with Tetracene

Ghosh

Budanović

et al. 2021

Asian J Org Chem

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“…After adding the acid, the sensor produced a new peak, and as the concentration of the acid increased, the intensity of the new peak increased, while the original fluorescence emission peak weakened slightly. This might have occurred because the hydrogen ions were ionized by the acid, which protonated CDs, and the amino groups on the surface of the CDs, resulting in a state more likely to occur fluorescence which was observed as an increase in the fluorescence intensity (Pang, et al., 2020; Tervola et al., 2020). Furthermore, it could be seen from Figure 4 that the response intensity of different acids to CDs was lactic acid > acetic acid > butyric acid > caproic acid.…”

Section: Resultsmentioning

confidence: 99%

Furfural and organic acid targeted carbon dot sensor array for the accurate identification of Chinese baijiu

Jia

Fan

et al. 2021

Journal of Food Science

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Baijiu quality control has always been a major challenge for researchers. In this paper, taking furfural which is closely related to baijiu brewing process and organic acids related to baijiu fermentation process and microorganism types as the main discriminating factors, a carbon dot (CDs) sensor array targeting furfural and organic acids was constructed to identify 41 kinds of baijiu. Through the fluorescence response investigation of CDs synthesized by isomers of benzenediol, aminophenol, and phenylenediamine to different baijiu, two CDs synthesized by meta‐benzene substitutions containing ‐NH2 were selected to build a fluorescence sensor array. Due to the aggregation‐induced enhancement effect between furfural and the CDs, and the protonation of organic acid and the CDs, different fluorescence changes were observed, the sensor array combined with partial least squares regression could quantitatively analyze furfural and organic acids. What is more, semi‐quantitative analysis of furfural and lactic acid in baijiu was performed. Owing to the interaction of the two CDs with furfural and organic acids in baijiu, the sensor array could accurately identify different baijiu through linear discriminant analysis. This sensor array has potential applications in the quantitative analysis of flavor substances in other alcoholic beverages, moreover, this method could provide a quick response and practical tool for real‐time quality control monitoring in the baijiu industry.

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“…, the stabilising power of the counter-anion involved in the protonation process. 32–34 In our previous studies, protonation significantly enhanced the fluorescence intensity of quinoline derivatives over 50-fold increasing the fluorescence quantum yield up to 30%. 32 Herein, the effect of the intermolecular interactions on the emission characteristics of the carbazole-based materials upon protonation both in solution and in the solid-state were investigated.…”

Section: Introductionmentioning

confidence: 81%

“…32–34 In our previous studies, protonation significantly enhanced the fluorescence intensity of quinoline derivatives over 50-fold increasing the fluorescence quantum yield up to 30%. 32 Herein, the effect of the intermolecular interactions on the emission characteristics of the carbazole-based materials upon protonation both in solution and in the solid-state were investigated. Protonation of L1 and L2 (Scheme 1) was found to facilitate the planarization of the pyridyl and the carbazole units, while hindering the complete rotation of the pyridyl moiety.…”

Section: Introductionmentioning

confidence: 81%

Protonation-induced fluorescence modulation of carbazole-based emitters

et al. 2022

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Fluorescence enhancement of quinolines by protonation

Abstract: The acid–base interactions of quinolines are studied in both liquid and solid-state to explore efficient tools for fluorescence enhancement.

Cited by 30 publications

References 44 publications

Synthesis of 5‐Azatetracene and Comparison of Its Optical and Electrochemical Properties with Tetracene

Synthesis of 5‐Azatetracene and Comparison of Its Optical and Electrochemical Properties with Tetracene

Furfural and organic acid targeted carbon dot sensor array for the accurate identification of Chinese baijiu

Protonation-induced fluorescence modulation of carbazole-based emitters

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