As an emerging class of photonic and electronic materials, glassy liquid crystals are capable of preserving in the solid state molecular order characteristic of liquid crystals. Because of superior chemical purity and favorable rheological properties, glassy liquid crystals can be readily processed into large-area monodomain films. This thesis aimed at deterministic synthesis of glassy chiral nematics, photochromic glassy nematics, and glassy discotics. The most significant contributions are recapitulated as follows: (1) Through deterministic synthesis of multifunctional materials via enzymatic and chemical approaches, enantiomeric glassy chiral nematics were prepared efficiently and shown to possess a glass transition temperature over 60°C and a cholesteric fluid temperature range wider than 100°C. Device concepts were also demonstrated for high-performance circular polarizers, notch filters and reflectors in the ultraviolet, across the visible, and to the infrared region. (2) The first photochromic glassy nematic liquid crystal was successfully designed, synthesized and characterized to possess a glass transition temperature over 100°C and a clearing point over 200°C. A large-area solid film was prepared through melt processing to demonstrate high-speed switching of anisotropic refractive indices and optical birefringence as a novel approach to rewritable optical memory and photonic switching in solid films. (3) Glassy discotic liquid crystals were synthesized and characterized by x-ray diffraction, polarizing optical microscopy, differential scanning calorimetry, and dynamic mechanical analysis to reveal sub-freezing glass transition temperatures. However, the absence of recrystallization at room temperature over a period of over four years was a manifestation of morphological stability of the discotics.
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