The dipole moment, its magnitude and orientation are important parameters in design of polar liquid crystals for electro-optical applications. In this context we have investigated two series of liquid crystals, 1 and 2, based on pyridinium derivatives of the [closo-1-CB9H10]- (A) and [closo-1-CB11H12]- (B) anions as high Δε polar materials for LCD applications. The C(1) substituted zwitterions 1A and 1B were obtained by reactions of 1-amino derivatives 3 with 4-alkoxypyrylium triflates.[1] The 10-pyridinium derivatives 2A were efficiently obtained by reacting 10-dinitrogen derivative of 4A with functionalized 4-alkoxypyridines.[2] The analogous pyridinium zwitterions 2B of the 12-vertex cluster were obtained by diazotization of amine 5B in the presence of 4-methoxypyridine and subsequent demethylation/O-alkylation sequence of the resulting 12-methoxypyridinium 6B to yield 2B.[3] The new methods were used to prepare liquid crystals, which were investigated by thermal, optical and dielectric methods. References: [1] Pecyna, J.; Pociecha, D.; Kaszynski, P. J. Mater. Chem. C 2014, 2, 1585. [2] Ringstrand, B.; Kaszynski, P. J. Mater. Chem. 2010, 20, 9613 [3] Pecyna, J.; Ringstrand, B.; Domagala, S.; Kaszynski, P.; Wozniak, K. Inorg. Chem. accepted; Pecyna, J.; Denicola, R. P.; Gray, H. M.; Ringstrand, B.; Kaszynski, P. Liq. Cryst. 2014, 41, 1188.

Polar liquid crystals based on pyridinium zwitterions of the [closo-1-CB9H10]- and [closo-1-CB11H12]- anions

249th National Meeting (2015)

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