TY - JOUR
T1 - Synthesis of a Zn-salen resorcinarene-based cavitand and its fluorescence response to nitro compounds
AU - Lee, Yujin
AU - Koo, Hyo Geun
AU - Jang, Seung Pyo
AU - Erdmann, Alan B.
AU - Vernetti, Samantha S.
AU - Kim, Cheal
AU - Harrison, Roger G.
PY - 2014
Y1 - 2014
N2 - The synthesis, spectroscopic characterisation, conformational switching and fluorescence quenching efficiency of a resorcinarene-based cavitand containing Zn-salen (Zn-Cav) are reported. Synthesis of Zn-Cav was accomplished by the condensation of a quinoxaline derivatised with Zn-salen and a resorcinarene-based cavitand containing three quinoxalines. 1H NMR spectroscopy confirmed that in DMSO, chloroform and acetone Zn-Cav resides in the vase conformation. The molecular geometry of Zn-Cav selectively changes from vase to kite under acidic conditions. Detection by fluorescence quenching of nitro-containing molecules, such as 4-nitrotoluene, 2,4-dinitrotoluene and 2,3-dimethyl-2,3-dinitrobutane was explored by spectrofluorimetry. It was found that the fluorescence of Zn-Cav is efficiently quenched by nitroaromatic compounds.
AB - The synthesis, spectroscopic characterisation, conformational switching and fluorescence quenching efficiency of a resorcinarene-based cavitand containing Zn-salen (Zn-Cav) are reported. Synthesis of Zn-Cav was accomplished by the condensation of a quinoxaline derivatised with Zn-salen and a resorcinarene-based cavitand containing three quinoxalines. 1H NMR spectroscopy confirmed that in DMSO, chloroform and acetone Zn-Cav resides in the vase conformation. The molecular geometry of Zn-Cav selectively changes from vase to kite under acidic conditions. Detection by fluorescence quenching of nitro-containing molecules, such as 4-nitrotoluene, 2,4-dinitrotoluene and 2,3-dimethyl-2,3-dinitrobutane was explored by spectrofluorimetry. It was found that the fluorescence of Zn-Cav is efficiently quenched by nitroaromatic compounds.
KW - dinitrotoluene
KW - fluorescence quenching
KW - molecular recognition
UR - https://www.scopus.com/pages/publications/84898041952
U2 - 10.1080/10610278.2013.852673
DO - 10.1080/10610278.2013.852673
M3 - Article
AN - SCOPUS:84898041952
SN - 1061-0278
VL - 26
SP - 245
EP - 250
JO - Supramolecular Chemistry
JF - Supramolecular Chemistry
IS - 3-4
ER -