Double Functional Group Transformations for Fluorescent Probe Construction: A Fluorescence Turn‐On Probe for Thioureas

Lin, Weiying; Cao, Xiaowei; Yuan, Lin; Ding, Yundi

doi:10.1002/chem.201000244

Cited by 10 publications

(9 citation statements)

References 30 publications

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“…However, 3‐acetylcoumarin derivatives were synthesized in solventless reaction condition under microwave irradiation (MWI) method as well as conventional methods (CM). In addition, for the synthesis of their brominated derivatives, both literature methods and our improved MWI method were used (Scheme ) , . The coumarin‐imidazo[1,2‐ a ]pyrimidines bearing bromine 19 and 20 were used to increase the length of the conjugation in coumarin‐imidazo[1,2‐ a ]pyrimidine derivatives, and a second family of compounds was obtained.…”

Section: Resultsmentioning

confidence: 99%

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Proton Sensitive Functional Organic Fluorescent Dyes Based on Coumarin‐imidazo[1,2‐a]pyrimidine; Syntheses, Photophysical Properties, and Investigation of Protonation Ability

Aydıner

Seferoğlu

2018

Eur J Org Chem

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A novel series of 2‐coumarin‐3‐yl‐imidazo[1,2‐a]pyrimidines have been synthesized with functionalized coumarin and pyrimidine units of the different architecture to give various fluorescent compounds. A new additional series bearing unsubstituted coumarin and 7‐dialkylaminocoumarin as fluorophore were obtained by palladium‐catalyzed cross‐coupling reactions, through coupling of 6‐bromo‐2‐coumarin‐3‐yl‐imidazopyrimidine derivatives with various arylboronic acids. In the all reaction step, microwave irradiation (MWI) method was used and compared with the conventional method (CM). Photophysical properties of synthesized compounds were studied by a combination of UV/Vis and fluorescence spectroscopy in various solvents having different polarities. The protonation abilities of all compounds were investigated by titration with trifluoroacetic acid (TFA) in dichloromethane. In both series, the compounds bearing 7‐dialkylaminocoumarin are fluorescently active even in daylight and showed maximum absorption wavelengths (λabs–max) in the visible region in all solvents used. In addition, they showed drastic color and emission change in acidic environment. Moreover, for the investigation of protonation ability of three selected compounds bearing 7‐dialkylaminocoumarin have been studied using a buffer solution with various pH and determinated their pKa values. The compound bearing morpholine has the potential to use as colorimetric and luminescence pH sensor. The thermal properties of all the synthesized compounds were also evaluated with TGA to test their usability as optic dyes.

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Section: Resultsmentioning

confidence: 99%

“…General Procedure for the Synthesis of 3‐(2‐Bromoacetyl)coumarin Derivatives. Method A: A mixture of 3‐acetylcoumarin derivative ( 4 , 5 and 6 ), (2 mmol), copper(II)bromide (4 mmol) was added to ethanol (15 mL) and refluxed for 12 hours. The mixture was cooled to room temperature and 2 mL of cold water was added.…”

Section: Methodsmentioning

confidence: 99%

Proton Sensitive Functional Organic Fluorescent Dyes Based on Coumarin‐imidazo[1,2‐a]pyrimidine; Syntheses, Photophysical Properties, and Investigation of Protonation Ability

Aydıner

Seferoğlu

2018

Eur J Org Chem

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“…We then applied the procedure reported by Lin et al [36] for the formation of 5 using CuBr 2 in excess as the bromine source, which we had initially viewed as a less attractive protocol. Gratifyingly, this procedure proved effective, although the target coumarin 5 was produced in a rather modest yield of 45% given the reaction stoichiometry (reported yield 47% [36]), with the only other material isolated from the crude reaction mixture being unreacted starting material and required labour 5 intensive chromatography to effect separation of the reaction mixture. This also allowed us to confirm the structure of 5 by single crystal X-ray diffraction, Figure 2b.…”

Section: Subsequent Repetition Of the Reaction Again Gave Complex MIXmentioning

confidence: 99%

“…CCDC reference 1453089. °C, 16 h [36] or Br 2 , HBr/AcOH [37,38]; ii) NaN 3 , THF, 45 °C, 18 h. Table 1. Summary of the reaction conditions employed for the synthesis of 2.…”

Section: Single Crystal X-ray Crystallographymentioning

confidence: 99%

An investigation into the synthesis of azido-functionalised coumarins for application in 1,3-dipolar “click” cycloaddition reactions

et al. 2016

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A range of reported methods have been assessed for the synthesis of two coumarin fluorophores containing azides, 1a and 2, for subsequent "click" modification. In the case of 1a reported methods were successfully applied, but the resulting azide proved to be rather unstable and appears more suited to in-situ generation and conversion to the "click" triazole. In the case of 2, reported methods for the synthesis of precursor 5 were ineffective in two cases and resulted in either no bromination -to the carbonyl or the formation of multiple unwanted side-products, some of which were isolated, 6-13. The use of CuBr 2 in excess or Br 2 in 50% HBr in acetic acid did result in the isolation of 5, which could be efficiently converted to 2 using excess NaN 3 in THF.

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“…A simple coumarin derivative 98 is the first fluorescence turn-on probe for thioureas by the double functional group transformation strategy. The probe exhibits high sensitivity and selectivity for thioureas over other structurally and chemically related species including urea and thiophenol (Lin et al, 2010b). The simple coumarin sensor 67 (Fig.…”

Section: Coumarin-derived Fluorescent Chemosensors For Thiolsmentioning

confidence: 99%

Coumarin-Derived Fluorescent Chemosensors

Li¹,

Cai²,

Chen³

2012

Advances in Chemical Sensors

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Double Functional Group Transformations for Fluorescent Probe Construction: A Fluorescence Turn‐On Probe for Thioureas

Cited by 10 publications

References 30 publications

Proton Sensitive Functional Organic Fluorescent Dyes Based on Coumarin‐imidazo[1,2‐a]pyrimidine; Syntheses, Photophysical Properties, and Investigation of Protonation Ability

Proton Sensitive Functional Organic Fluorescent Dyes Based on Coumarin‐imidazo[1,2‐a]pyrimidine; Syntheses, Photophysical Properties, and Investigation of Protonation Ability

An investigation into the synthesis of azido-functionalised coumarins for application in 1,3-dipolar “click” cycloaddition reactions

Coumarin-Derived Fluorescent Chemosensors

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