Strapped calix[4]pyrroles bearing a 1,3-indanedione at a beta-pyrrolic position: chemodosimeters for the cyanide anion.
A strapped calix[4]pyrrole bearing a 1,3-indanedione group at a beta-pyrrolic position has been synthesized and studied as a ratiometric cyanide-selective chemosensor. A concentration-dependent bleaching of the initial yellow color was observed upon addition of the cyanide anion. The bleaching, which was observed exclusively with the cyanide anion, occurred even in the presence of other anions. Spectroscopic studies provide support for a mechanistic interpretation wherein the cyanide anion forms a complex with the receptor (K = 2.78 x 10(4) M(-1)) through a fast equilibrium, which is followed by slow nucleophilic addition to the beta-position of the 1,3-indanedione group. A minimum inhibitory effect from other anions was observed, a feature that could be beneficial in the selective sensing of the cyanide anion.
Kim
Sook-Hee
SH
Department of Chemistry and Institute of Molecular Science & Fusion Technology, Kangwon National University, Chun-Chon 200-701, Korea.
Hong
Seong-Jin
SJ
Yoo
Jaeduk
J
Kim
Sung Kuk
SK
Sessler
Janathan L
JL
Lee
Chang-Hee
CH
D000838:Anions; D047250:Calixarenes / Q000138:chemical synthesis* / Q000737:chemistry; D003124:Colorimetry; D007189:Indans / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000032:analysis / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
C413384:1,2-indanedione; D000838:Anions; D007189:Indans; D009570:Nitriles; D011758:Pyrroles; D047250:Calixarenes