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2-(Alkylamino)-3-aryl-6,7-dihydrobenzofuran-4(5H)-ones: Improved Synthesis and their Photophysical Properties.

Kumar M, Kumawat LK, Gupta VK, Sharma A - ChemistryOpen (2015)

Bottom Line: As such, improved synthetic access to furans is an important research goal.This method is significantly improved from previously described protocols in terms of applicability of wide ranging aryl aldehydes, better yields, shorter reaction times, facile work up and essentially no need of column chromatography.Further studies to investigate the UV absorption and luminescence behavior of these compounds revealed their utility as "naked-eye sensors" for aluminum detection.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Indian Institute of Technology Roorkee Roorkee, Uttarakhand, 247667, India.

ABSTRACT
Furans are an important class of compounds and exhibit a diverse range of activities and properties. As such, improved synthetic access to furans is an important research goal. In the present report, a solvent- and catalyst-free reaction between 5,5-dimethyl-1,3-cyclohexanedione (dimedone), an aryl aldehyde and an isocyanide under microwave irradiation is presented. This method is significantly improved from previously described protocols in terms of applicability of wide ranging aryl aldehydes, better yields, shorter reaction times, facile work up and essentially no need of column chromatography. The photophysical properties of this series of compounds were studied for their possible applicability in the field of metal ion sensors. In solution, two compounds, 2-(cyclohexylamino)-3-(1H-indol-3-yl)-6,6-dimethyl-6,7-dihydrobenzofuran-4(5H)-one (1 i) and 2-(tert-butylamino)-3-(1H-indol-3-yl)-6,6-dimethyl-6,7-dihydrobenzofuran-4(5H)-one (1 j), underwent an observable color change from yellow to colorless in the presence of aluminum(III) ions. Further studies to investigate the UV absorption and luminescence behavior of these compounds revealed their utility as "naked-eye sensors" for aluminum detection.

No MeSH data available.


Related in: MedlinePlus

Fluorescence emission changes (at 5.0×10−5 m) upon addition of different metal ions for compounds A) 1 i (λex=417 nm) and B) 1 j (λex=412 nm) in methanol at pH 7.0.
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fig02: Fluorescence emission changes (at 5.0×10−5 m) upon addition of different metal ions for compounds A) 1 i (λex=417 nm) and B) 1 j (λex=412 nm) in methanol at pH 7.0.

Mentions: Extensive UV and fluorescence studies were carried out, and the absorption and emission maxima, and molar extinction coefficients in methanol are presented in Table 4 (also see Figures SS1 and SS2 in the Supporting Information). The absorption and emission spectra of all compounds were also recorded in the presence of different metals: AgI, AlIII, CaII, CdII, CrIII, CuII, FeIII, CoII, InIII, MgII, MnII, NaI, NiII, PbII and ZnII. Of the 13 compounds investigated, two compounds (1 i and 1 j) exhibited a striking color change, from yellow to colorless (turn-off colorimetric sensing), in the UV absorption and fluorescence spectra when in the presence of aluminum metal. Hence, these two candidates were undertaken forward for full investigation (Figure 2 A,B).


2-(Alkylamino)-3-aryl-6,7-dihydrobenzofuran-4(5H)-ones: Improved Synthesis and their Photophysical Properties.

Kumar M, Kumawat LK, Gupta VK, Sharma A - ChemistryOpen (2015)

Fluorescence emission changes (at 5.0×10−5 m) upon addition of different metal ions for compounds A) 1 i (λex=417 nm) and B) 1 j (λex=412 nm) in methanol at pH 7.0.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4608531&req=5

fig02: Fluorescence emission changes (at 5.0×10−5 m) upon addition of different metal ions for compounds A) 1 i (λex=417 nm) and B) 1 j (λex=412 nm) in methanol at pH 7.0.
Mentions: Extensive UV and fluorescence studies were carried out, and the absorption and emission maxima, and molar extinction coefficients in methanol are presented in Table 4 (also see Figures SS1 and SS2 in the Supporting Information). The absorption and emission spectra of all compounds were also recorded in the presence of different metals: AgI, AlIII, CaII, CdII, CrIII, CuII, FeIII, CoII, InIII, MgII, MnII, NaI, NiII, PbII and ZnII. Of the 13 compounds investigated, two compounds (1 i and 1 j) exhibited a striking color change, from yellow to colorless (turn-off colorimetric sensing), in the UV absorption and fluorescence spectra when in the presence of aluminum metal. Hence, these two candidates were undertaken forward for full investigation (Figure 2 A,B).

Bottom Line: As such, improved synthetic access to furans is an important research goal.This method is significantly improved from previously described protocols in terms of applicability of wide ranging aryl aldehydes, better yields, shorter reaction times, facile work up and essentially no need of column chromatography.Further studies to investigate the UV absorption and luminescence behavior of these compounds revealed their utility as "naked-eye sensors" for aluminum detection.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Indian Institute of Technology Roorkee Roorkee, Uttarakhand, 247667, India.

ABSTRACT
Furans are an important class of compounds and exhibit a diverse range of activities and properties. As such, improved synthetic access to furans is an important research goal. In the present report, a solvent- and catalyst-free reaction between 5,5-dimethyl-1,3-cyclohexanedione (dimedone), an aryl aldehyde and an isocyanide under microwave irradiation is presented. This method is significantly improved from previously described protocols in terms of applicability of wide ranging aryl aldehydes, better yields, shorter reaction times, facile work up and essentially no need of column chromatography. The photophysical properties of this series of compounds were studied for their possible applicability in the field of metal ion sensors. In solution, two compounds, 2-(cyclohexylamino)-3-(1H-indol-3-yl)-6,6-dimethyl-6,7-dihydrobenzofuran-4(5H)-one (1 i) and 2-(tert-butylamino)-3-(1H-indol-3-yl)-6,6-dimethyl-6,7-dihydrobenzofuran-4(5H)-one (1 j), underwent an observable color change from yellow to colorless in the presence of aluminum(III) ions. Further studies to investigate the UV absorption and luminescence behavior of these compounds revealed their utility as "naked-eye sensors" for aluminum detection.

No MeSH data available.


Related in: MedlinePlus