TY - JOUR
T1 - Anion responsive TTF-appended calix[4]arenes. synthesis and study of two different conformers
AU - Lee, Min Hee
AU - Cao, Qian Yong
AU - Kim, Sung Kuk
AU - Sessler, Jonathan L.
AU - Kim, Jong Seung
PY - 2011/2/4
Y1 - 2011/2/4
N2 - Two new cone- and 1,3-alternate-calix[4]arenes (cone-1 and 1,3-alt-1), bearing four modified TTF (tetrathiafulvalene) substituents on the upper rim, have been synthesized. The binding ability of these two sets of conformers for various anions, including F-, Cl-, Br-, I -, PF6-, ClO4-, HSO 4-, CH3COO-, H2PO 4-, and HP2O7 3 -, was tested in organic media by monitoring the changes in their UV/vis and 1H NMR spectra as a function of added anion, as well as via cyclovoltammetry (CV) (all anions studied as their respective TBA salts). On the basis of the present findings, we propose that incorporation of four TTF units within an overall calix[4]arene-based recognition framework produces a preorganized receptor system that displays a modest preference for the pyrophosphate (HP2O7 3-)anion.
AB - Two new cone- and 1,3-alternate-calix[4]arenes (cone-1 and 1,3-alt-1), bearing four modified TTF (tetrathiafulvalene) substituents on the upper rim, have been synthesized. The binding ability of these two sets of conformers for various anions, including F-, Cl-, Br-, I -, PF6-, ClO4-, HSO 4-, CH3COO-, H2PO 4-, and HP2O7 3 -, was tested in organic media by monitoring the changes in their UV/vis and 1H NMR spectra as a function of added anion, as well as via cyclovoltammetry (CV) (all anions studied as their respective TBA salts). On the basis of the present findings, we propose that incorporation of four TTF units within an overall calix[4]arene-based recognition framework produces a preorganized receptor system that displays a modest preference for the pyrophosphate (HP2O7 3-)anion.
UR - http://www.scopus.com/inward/record.url?scp=79851500290&partnerID=8YFLogxK
U2 - 10.1021/jo1021713
DO - 10.1021/jo1021713
M3 - Article
C2 - 21194202
AN - SCOPUS:79851500290
SN - 0022-3263
VL - 76
SP - 870
EP - 874
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 3
ER -