TY - JOUR
T1 - 4′-Bromo-2′,3′,5′,6′-tetrafluorostilbazole
T2 - Donor and acceptor site for halogen bonding and π-stacking in one rigid-rod-type molecule
AU - Lucassen, André C.B.
AU - Vartanian, Maida
AU - Leitus, Gregory
AU - Van Der Boom, Milko E.
PY - 2005/9
Y1 - 2005/9
N2 - The title compound, a new fluorinated stilbazole-based chromophore combines hydrocarbon (HC) donor and perfluorocarbon (PFC) acceptor sites in one rigid-rod-type conjugated molecule. The bifunctional stilbazole derivative combines several possibilities of weak, medium, and strong intermolecular interactions leading to an attractive crystal packing. The chromophore shows strong π-π stacking behavior in solution, while its crystal structure consists of an infinite unimolecular network involving both interchain π-π stacking and N⋯Br halogen bonding. The latter Lewis acid-base interactions do not play a dominant role in controlling the solution optical properties. In the solid state, the molecules are aligned in one-dimensional infinite head-to-tail chains as a result of attractive halogen bonding. Adjacent chains are oriented in opposite directions.
AB - The title compound, a new fluorinated stilbazole-based chromophore combines hydrocarbon (HC) donor and perfluorocarbon (PFC) acceptor sites in one rigid-rod-type conjugated molecule. The bifunctional stilbazole derivative combines several possibilities of weak, medium, and strong intermolecular interactions leading to an attractive crystal packing. The chromophore shows strong π-π stacking behavior in solution, while its crystal structure consists of an infinite unimolecular network involving both interchain π-π stacking and N⋯Br halogen bonding. The latter Lewis acid-base interactions do not play a dominant role in controlling the solution optical properties. In the solid state, the molecules are aligned in one-dimensional infinite head-to-tail chains as a result of attractive halogen bonding. Adjacent chains are oriented in opposite directions.
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U2 - 10.1021/cg0501433
DO - 10.1021/cg0501433
M3 - Article
AN - SCOPUS:25444483107
VL - 5
SP - 1671
EP - 1673
JO - Crystal Growth and Design
JF - Crystal Growth and Design
SN - 1528-7483
IS - 5
ER -