Limits...
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.


Competitive selectivity of probes A) 1 i (λmax=417 nm) and B) 1 j (λmax=412 nm) toward various metal ions (1.0 equiv). The emission intensity of probe in the presence of AlIII ions (▪) and in the presence of AlIII and other metal ions (▪).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4608531&req=5

fig03: Competitive selectivity of probes A) 1 i (λmax=417 nm) and B) 1 j (λmax=412 nm) toward various metal ions (1.0 equiv). The emission intensity of probe in the presence of AlIII ions (▪) and in the presence of AlIII and other metal ions (▪).

Mentions: Since selectivity is important for potential applicability as a sensor, an interference study was conducted to measure the influence of other metal ions on the AlIII binding by ligands 1 i and 1 j. Gratifyingly, with the exception of CdII and NiII, the presence of no other metal produced any significant change in the fluorescent spectra of the compounds (Figure 3 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)

Competitive selectivity of probes A) 1 i (λmax=417 nm) and B) 1 j (λmax=412 nm) toward various metal ions (1.0 equiv). The emission intensity of probe in the presence of AlIII ions (▪) and in the presence of AlIII and other metal ions (▪).
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig03: Competitive selectivity of probes A) 1 i (λmax=417 nm) and B) 1 j (λmax=412 nm) toward various metal ions (1.0 equiv). The emission intensity of probe in the presence of AlIII ions (▪) and in the presence of AlIII and other metal ions (▪).
Mentions: Since selectivity is important for potential applicability as a sensor, an interference study was conducted to measure the influence of other metal ions on the AlIII binding by ligands 1 i and 1 j. Gratifyingly, with the exception of CdII and NiII, the presence of no other metal produced any significant change in the fluorescent spectra of the compounds (Figure 3 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.