TY - JOUR
T1 - Locked energy of axial to equatorial transformation monitored by exciplex and excimer fluorescence
AU - Kadirvel, Manikandan
AU - Bichenkova, Elena V.
AU - D'Emanuele, Antony
AU - Freeman, Sally
PY - 2006/8/5
Y1 - 2006/8/5
N2 - 2-O-tert-Butyldimethylsilyl-4,6-bispyrenoyl-myo-inositol-1,3,5-orthoformate (1) and 2-O-tert-butyldimethylsilyl-4-[(4-dimethylamino)benzoyl]-6-pyrenoyl- myo-inositol-1,3,5-orthoacetate (2) adopt unstable chair conformations with five substituents axial, in which the aromatic esters participate in π-stacking, and give excimer and exciplex fluorescence, respectively. Upon addition of acid, the orthoformate/orthoacetate lock is cleaved, which allows the inositol ring to switch to the more stable penta-equatorial chair conformation, with loss of exciplex/excimer fluorescence. Copyright © 2006 The Chemical Society of Japan.
AB - 2-O-tert-Butyldimethylsilyl-4,6-bispyrenoyl-myo-inositol-1,3,5-orthoformate (1) and 2-O-tert-butyldimethylsilyl-4-[(4-dimethylamino)benzoyl]-6-pyrenoyl- myo-inositol-1,3,5-orthoacetate (2) adopt unstable chair conformations with five substituents axial, in which the aromatic esters participate in π-stacking, and give excimer and exciplex fluorescence, respectively. Upon addition of acid, the orthoformate/orthoacetate lock is cleaved, which allows the inositol ring to switch to the more stable penta-equatorial chair conformation, with loss of exciplex/excimer fluorescence. Copyright © 2006 The Chemical Society of Japan.
U2 - 10.1246/cl.2006.868
DO - 10.1246/cl.2006.868
M3 - Article
SN - 1348-0715
VL - 35
SP - 868
EP - 869
JO - Chemistry Letters
JF - Chemistry Letters
IS - 8
ER -