by Qian Wang. / Thesis (Ph.D.)--Chinese University of Hong Kong, 1992. / Includes bibliographical references (leaves 107-111). / Acknowledgements --- p.i / Contents --- p.ii / Abstract --- p.iv / Chapter I. --- Introduction --- p.1 / Chapter II. --- Results and Discussion --- p.23 / Chapter II-1. --- "Stereoselective Synthesis of Chiral Liquid Crystalline Compounds Containing a 1,4-Disubstituted Cyclohexene Ring" --- p.23 / Chapter II-1-1. --- "Synthesis of (S)-(-)- and (R)-(+)-4'-(4""-Cyanobiphenyl) 4-Pentyl-3-cyclohexene-1-carboxylate (1 and 3) and (S)-(-)-4'-(4""-Octoxybiphenyl) 4-Pentyl-3-cyclohexene-1-carboxylate (2)" --- p.23 / Chapter II-1-2. --- "Synthesis of (S)-(-)-4'-(4""-Cyanobiphenyl) 4-Butoxymethyl-3-cyclohexene-1-carboxylate (4)" --- p.35 / Chapter II-1-3. --- "Synthesis of (S)-(-)- and (R)-(+)-4'-(4""-Heptoxybiphenyl) 4-(2-Propenyl)-1-cyclohexene-1-carboxylate (5 and 7) and (S)-(-)- and (R)-(+)-4'-(4""-Octoxybiphenyl) 4-(2-Propenyl)-1-cyclohexene-1-carboxylate (6 and 8)" --- p.37 / Chapter II-2. --- "Synthesis of Chiral Liquid Crystalline Compound Containing a trans-2,5-Disusbstituted Cyclohexanone Ring´ؤ(1S,4S)-4'-(4""-Heptoxybiphenyl) 4-Penyl-3-cyclohexanone-1-carboxylate (9)" --- p.42 / Chapter II-3. --- "Determination of Enantiomeric Purities of (S)-(-)- and (R)-(+)-Perillalcohols (17 and 28), (S)-(-)- and (R)-(+)-1-Pentyl-4-hydroxymethyl-l-cyclohexenes(35 and 36), and (2S,5S)-2-Pentyl-5-hydroxymethyl-l-cyclohexanone (64)" --- p.58 / Chapter II-3-1. --- Determination of Enantiomeric Purities of (S)-(-)- and (R)-(+)-Perillalcohols (17 and 28) --- p.58 / Chapter II-3-2. --- Determination of Enantiomeric Purities of (S)-(-)- and (R)-(+)-1-Pentyl-4-hydroxymethyl-1-cyclohexenes (35 and36) --- p.64 / Chapter II-3-3. --- "Determination of Enantiomeric Purity of (2S,5S)-2-Pentyl-5-hydroxymethyl-1 -cyclohexanone (64)." --- p.67 / Chapter II-4. --- "Mesomorphic Phases and Transition Temperatures of Chiral Liquid Crystalline Compounds 2, 3, 5, 6, 7, 8 and 9" --- p.72 / Chapter III. --- Conclusion --- p.77 / Chapter IV. --- Experimental --- p.78 / Chapter V. --- References --- p.107 / List of Spectra --- p.112 / Spectra --- p.116

Perylene-based materials, including charge-transport discotic liquid crystals and charge-transfer long-wavelength absorbing chromophores, for potential organic electronic and optoelectronic applications, were designed, synthesized and characterized. Two types of discotic liquid crystals, perylene diimides and coronene diimides, can form columnar liquid crystalline phases over a wide temperature range; many of them can have room-temperature liquid crystalline phases after cooling from isotropic liquid. Their charge transport properties were studied by space-charge limited current method; high charge carrier mobilities, with the highest being up to 6.6 cm2/Vs, were found in liquid crystalline phases of these materials under ambient conditions. Structural variables, including aromatic cores and side groups, were examined to get a certain degree of understanding of charge transport properties in these discotic liquid crystals. It was found that mesophase order can have an important effect on charge carrier mobilities. The discotic liquid crystals with high charge carrier mobilities are serious candidates for use in large-area low-cost applications such as solar cells. Long-wavelength, highly absorbing chromophores, featuring donor-substituted perylene diimides, were generated by a combination of charge-transfer process and conjugation extension. The charge-transfer chromophores are expected to lead to further investigation on their potentials as sensitizers in Grtzel solar cells.