Self-Complementary Nonlinear Optical-Phores Targeted to Halogen Bond-Driven Self-Assembly of Electro-Optic Materials
Cryst. Growth Des. 2011, 11, 5642?5648
E. Cariati, G. Cavallo, A. Forni, G. Leem, P. Metrangolo, F. Meyer, T. Pilati, G. Resnati, S. Righetto, G. Terraneo, E. Tordin
Figure 1. A ball-and-stick view down the crystallographic a axis of the infinite 1D halogen-bonded chains in the crystal packing of the self-complementary XB-based tecton 1. Colors as follows: C, dark gray; H, light gray; F, green; I, purple; N, blue; XB, dotted black lines.
Figure 1. A ball-and-stick view down the crystallographic a axis of the infinite 1D halogen-bonded chains in the crystal packing of the self-complementary XB-based tecton 1. Colors as follows: C, dark gray; H, light gray; F, green; I, purple; N, blue; XB, dotted black lines.
ABSTRACT
Three new push pull molecules having either pyridyl or N, N-dimethylanilino groups as electron-donor moieties and the p-iodotetrafluorophenyl ring as an electron-acceptor group have been synthesized and their single crystal X-ray structures are reported. Halogen bonding drives the self-assembly of these molecules in the solid state giving rise to head-to-tail halogen-bonded infinite polar chains which crystallize in an antiparallel arrangement. The three new nonlinear optical (NLO)-phores synthesized show high hyperpolarizabilities at the molecular level in solution. Rationalization of the obtained NLO measurements is supported by molecular modeling calculations.