Selective and sensitive detection of mercuric ion by novel dansyl-appended calix[4] arene molecules, via fluorescence quenching
View Patent ↗In particular, Compounds of Formula I or Formula II, generally known as calix[4]arenes, may be prepared. The compounds may be used to test samples for the presence of Hg 2+ by fluorescence quenching. The compounds may also be used to selectively detect Hg 2+ in samples containing other mono- or divalent metals.
1. A compound having Formula I or Formula II:
wherein:
R 1 is H, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
R 2 is H, CH 2 C(O)OR 4 , or a group of formula
R 3 and R 6 are individually a group of formula
R 4 is methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, or tert-butyl; and
R 5 is methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, or tert-butyl.
2. The compound of claim 1 that is Formula I, wherein R 1 is H; R 2 is CH 2 C(O)OR 4 ; R 4 is ethyl; and R 5 is methyl.
3. The compound of claim 1 that is Formula I, wherein R 1 is H; R 2 is H; and R 5 is methyl.
4. The compound of claim 1 that is Formula I, wherein R 1 is H; R 2 is a group of formula
and R 5 is methyl.
5. The compound of claim 1 that is Formula I, wherein R 1 is tert-butyl; R 2 is H; and R 5 is methyl.
6. The compound of claim 1 that is Formula I, wherein R 1 is tert-butyl; R 2 is CH 2 C(O)OR 4 ; R 4 ethyl; and R 5 is methyl.
7. The compound of claim 1 that is Formula II, wherein R 5 is methyl.
8. A complex comprising the compound of Formula I or Formula II according to claim 1 and a Hg 2+ ion.
9. A complex comprising the compound of claim 3 and a Hg 2+ ion.
10. A complex comprising the compound of claim 5 and a Hg 2+ ion.
11. A method of testing for the presence of Hg 2+ comprising:
detecting the fluorescence of a test sample comprising a compound of claim 1 ; and
comparing the detected fluorescence of the test sample to that of a control sample;
wherein:
a reduction in fluorescence of the test sample relative to the control sample indicates the presence of Hg 2+ in the sample.
12. The method of claim 11 , wherein the method selectively detects the presence of Hg 2+ in the presence of one or more different divalent metal ions in the sample.
13. The method of claim 12 , wherein the one or more different divalent metal ions are selected from the group consisting of Ca 2+ , Cd 2+ , Co 2+ , Cu 2+ , Fe 2+ , Mg 2+ , Mn 2+ , Ni 2+ , Pb 2+ , and Zn 2+ .
14. A method of testing for the presence of Hg 2+ comprising:
preparing a test sample comprising a compound of claim 1 ;
detecting the fluorescence of the test sample, and
comparing the detected fluorescence of the test sample to that of a control sample,
wherein a reduction in fluorescence of the test sample relative to the control sample indicates the presence of Hg 2+ in the test sample.
15. A method of preparing a compound of Formula I comprising:
adding a compound of formula XSO 2 R 3 to a solution of a compound of Formula III, in the presence of a Lewis base;
wherein:
R 1 is H, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
R 2 is H, CH 2 C(O)OR 4 , or a group of formula
R 3 is a group of formula
R 4 is methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, or tert-butyl; and
R 5 is methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, or tert-butyl.
16. The method of claim 15 , wherein the Lewis base is a tertiary amine or pyridine.
17. A method of preparing a compound of Formula II comprising:
adding a compound of formula XSO 2 R 3 to a solution of a compound of Formula IV, in the presence of a Lewis base;
wherein:
R 6 is a group of formula
and R 5 is methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, or tert-butyl.
18. The method of claim 17 , wherein the Lewis base is a tertiary amine or pyridine.
19. The method of claim 17 , wherein the compound has stereoconformation: