Pyreno[2,1-b]pyrrole and bis(pyreno[2,1-b]pyrrole) as selective chemosensors of fluoride ion: a mechanistic study.
Pyreno[2,1-b]pyrrole and its dimeric derivative display excellent selectivity and sensitivity for detection of fluoride ion, in comparison with chloride, bromide, iodide, acetate, dihydrogen phosphate, hydrogen sulfate, perchlorate, nitrate, and thiocyanate ions. The hydrogen bonding with fluoride ion, both in formation and in subsequent dissociation, provides remarkable colorimetric and fluorescent changes in the visible region that are advantageous for real-time and on-site application. Detailed NMR and dynamic fluorescence spectroscopic analyses establish the associated mechanism.
Lin
Chia-I
CI
Department of Chemistry, National Taiwan University, Taipei 106, Taiwan.
Selvi
Srinivasan
S
Fang
Jim-Min
JM
Chou
Pi-Tai
PT
Lai
Chin-Hung
CH
Cheng
Yi-Ming
YM
D002625:Chemistry, Organic / Q000379:methods*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D005459:Fluorides / Q000032:analysis*; D006860:Hydrogen Bonding; D007477:Ions; D009682:Magnetic Resonance Spectroscopy; D019563:Mechanics; D011721:Pyrenes / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D012680:Sensitivity and Specificity; D012997:Solvents; D013050:Spectrometry, Fluorescence; D017186:Titrimetry
D007477:Ions; D011721:Pyrenes; C520775:Pyreno(2,1-b)pyrrole; D011758:Pyrroles; D012997:Solvents; C520776:bis(pyreno(2,1-b)pyrrole); D005459:Fluorides; D004121:Dimethyl Sulfoxide