Liquid Crystalline Magneto-Optically Active Peralkylated Azacoronene

Organic Faraday rotators have gained significant attention in recent years as a promising alternative to traditional inorganic magneto-optical (MO) materials as a result of their lower cost, superior mechanical properties, and potential for large-scale deployment. This interest is peaked by the fact that a number of high symmetry, rigid, strongly optically absorbing organic chromophores display Verdet constants an order of magnitude higher than commercial inorganic Faraday rotators. Critical to the development of new generations of organic materials is the ability to organize them in optimal structures for optical coupling/measurements. We report herein the synthesis of a dodecyl-substituted hexapyrrolohexaazacoronene (C) displaying discotic liquid crystalline (LC) properties and large Faraday rotation. Thin films with a redox mixed C/C composition display a discotic columnar LC phase, are stable to air and moisture in the solid and solution states, and achieve a maximum Verdet constant of 3.36 × 10⁵ deg T^-1 m^-1 at 700 nm. This result is consistent with Serber's model of magnetic circular birefringence and displays one of the largest reported Verdet constants for organic materials in the UV-Vis range. The LC phase aligns the molecules and leads to gains in Verdet constants of up to 105% through the favorable orientation of the molecules' magnetic and electric transition dipole moments with respect to the applied magnetic field.