TY - JOUR
T1 - Self-assembly of grid and helical hydrogen-bonded arrays incorporating bowl-shaped receptor sites that bind globular molecules
AU - Hardie, Michaele J.
AU - Godfrey, Peter D.
AU - Raston, Colin L.
PY - 1999/1/1
Y1 - 1999/1/1
N2 - 1,2-Dicarbadodecaborane(12) (o-carborane) and bowl-shaped cyclotriveratrylene (CTV) self-assemble through bifurcated C-Hcarborane ⋯ (O)2 hydrogen bonds into infinite arrays with two-dimensional (2D) hexagonal grid or helical chain topologies. The in-built shape-specific receptor sites bind o-carborane or fullerene C70. The structures of two such supramolecular systems in the solid state were established: (o-carborane)2(CTV) features hydrogenbonded carborane ⋯ CTV hexagonal grids as well as CTV ⋯ carborane host-guest interactions, while a helical hydrogen-bonded carborane ⋯ CTV chain is formed in the quaternary system (C70)(o-carborane)(CTV)(1,2-dichlorobenzene) in addition to CTV ⋯ C70 host-guest interactions. The bifurcated C-Hcarborane ⋯ (O)2 hydrogen bonding interaction common to both these structures was studied on the model system (o-carborane)(1,2-dimethoxybenzene) using ab initio calculations and found to be energetically favoured by 5.48 kcal mol-1, whereas a B-Hcarborane ⋯ (O), bifurcated hydrogen bonding was less favoured at 1.13 kcal mol-1.
AB - 1,2-Dicarbadodecaborane(12) (o-carborane) and bowl-shaped cyclotriveratrylene (CTV) self-assemble through bifurcated C-Hcarborane ⋯ (O)2 hydrogen bonds into infinite arrays with two-dimensional (2D) hexagonal grid or helical chain topologies. The in-built shape-specific receptor sites bind o-carborane or fullerene C70. The structures of two such supramolecular systems in the solid state were established: (o-carborane)2(CTV) features hydrogenbonded carborane ⋯ CTV hexagonal grids as well as CTV ⋯ carborane host-guest interactions, while a helical hydrogen-bonded carborane ⋯ CTV chain is formed in the quaternary system (C70)(o-carborane)(CTV)(1,2-dichlorobenzene) in addition to CTV ⋯ C70 host-guest interactions. The bifurcated C-Hcarborane ⋯ (O)2 hydrogen bonding interaction common to both these structures was studied on the model system (o-carborane)(1,2-dimethoxybenzene) using ab initio calculations and found to be energetically favoured by 5.48 kcal mol-1, whereas a B-Hcarborane ⋯ (O), bifurcated hydrogen bonding was less favoured at 1.13 kcal mol-1.
KW - Ab initio calculations
KW - Carboranes
KW - Crystal engineering
KW - Fullerenes
KW - Host-guest chemistry
UR - http://www.scopus.com/inward/record.url?scp=0032977477&partnerID=8YFLogxK
U2 - 10.1002/(SICI)1521-3765(19990604)5:6<1828::AID-CHEM1828>3.0.CO;2-P
DO - 10.1002/(SICI)1521-3765(19990604)5:6<1828::AID-CHEM1828>3.0.CO;2-P
M3 - Article
AN - SCOPUS:0032977477
SN - 0947-6539
VL - 5
SP - 1828
EP - 1833
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 6
ER -