Chiral periodic mesoporous organosilicates based on axially chiral monomers: transmission of chirality in the solid state.
Chiral mesoporous materials have been prepared with purely organic monomers employing an enantiomerically pure biphenyl bis-siloxane as a dopant along with simple 4,4'-bis(triethoxysilyl)biphenyl as the bulk material. Analysis of these materials by CD spectroscopy indicates the formation of new chiral aggregates in the solid state consistent with charge delocalization from adjacent aryl rings in close contact. These aggregates are only observed when the biphenyl and enantiomerically pure biaryl are both present. The red-shift resulting of the CD signal resulting from these interactions is modeled computationally using time-dependent DFT calculations.
MacQuarrie
Stephanie
S
Department of Chemistry, Queen's University, 90 Bader Lane, Kingston, Ontario, Canada K7L 3N6.
Thompson
Matthew P
MP
Blanc
Alexandre
A
Mosey
Nicholas J
NJ
Lemieux
Robert P
RP
Crudden
Cathleen M
CM
D001713:Biphenyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D003198:Computer Simulation; D019281:Dimerization; D008956:Models, Chemical; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010316:Particle Size; D016062:Porosity; D011789:Quantum Theory; D013237:Stereoisomerism; D013499:Surface Properties
D001713:Biphenyl Compounds; D017646:Organosilicon Compounds