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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.


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Effect of pH on sensing behavior of compounds 1 i and 1 j in the presence (1 i: •; 1 j: ▾) or in the absence (1 i: ▪; 1 j: ▴) of AlIII ions.
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fig06: Effect of pH on sensing behavior of compounds 1 i and 1 j in the presence (1 i: •; 1 j: ▾) or in the absence (1 i: ▪; 1 j: ▴) of AlIII ions.

Mentions: Finally, the influence of H+ ion concentration on sensitivity of both sensors was examined in aqueous methanolic solution at different pH levels. Both compounds retained their sensing abilities in mildly acidic to mildly basic media (Figure 6).


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)

Effect of pH on sensing behavior of compounds 1 i and 1 j in the presence (1 i: •; 1 j: ▾) or in the absence (1 i: ▪; 1 j: ▴) of AlIII ions.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig06: Effect of pH on sensing behavior of compounds 1 i and 1 j in the presence (1 i: •; 1 j: ▾) or in the absence (1 i: ▪; 1 j: ▴) of AlIII ions.
Mentions: Finally, the influence of H+ ion concentration on sensitivity of both sensors was examined in aqueous methanolic solution at different pH levels. Both compounds retained their sensing abilities in mildly acidic to mildly basic media (Figure 6).

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