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.


Job's plot to determine binding stoichiometry for compounds 1 i (•) and 1 j (▪).
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig04: Job's plot to determine binding stoichiometry for compounds 1 i (•) and 1 j (▪).

Mentions: Job's plot experiments were performed for both compounds 1 i and 1 j at around 415 nm in order to understand the characteristics and stoichiometry of binding (Figure 4). Intensity maxima were observed when the molar fraction of aluminum reached a value of 0.5, indicating a 1:1 stoichiometric complexion between the ligand (1 i or 1 j) and ion (i.e., AlIII). This fact was further supported by the results of high-resolution mass spectrometry (HRMS) (Figures SS13 and SS14 in the Supporting Information). Based on the absorbance and fluorescence titration data, Benesi–Hilderbrand plots47 were drawn for both compounds with aluminum ion (Figure 5 A,B). All of the data and related association constants are included in Table 5.


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)

Job's plot to determine binding stoichiometry for compounds 1 i (•) and 1 j (▪).
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig04: Job's plot to determine binding stoichiometry for compounds 1 i (•) and 1 j (▪).
Mentions: Job's plot experiments were performed for both compounds 1 i and 1 j at around 415 nm in order to understand the characteristics and stoichiometry of binding (Figure 4). Intensity maxima were observed when the molar fraction of aluminum reached a value of 0.5, indicating a 1:1 stoichiometric complexion between the ligand (1 i or 1 j) and ion (i.e., AlIII). This fact was further supported by the results of high-resolution mass spectrometry (HRMS) (Figures SS13 and SS14 in the Supporting Information). Based on the absorbance and fluorescence titration data, Benesi–Hilderbrand plots47 were drawn for both compounds with aluminum ion (Figure 5 A,B). All of the data and related association constants are included in Table 5.

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.