Mo Kai For. / Thesis submitted in: November 2001. / Thesis (M.Phil.)--Chinese University of Hong Kong, 2002. / Includes bibliographical references (leaves 78-81). / Abstracts in English and Chinese. / Contents --- p.i / Acknowledgement --- p.iii / Abstract --- p.iv / Chapter I --- Introduction --- p.1 / Chapter II --- Results and Discussion --- p.14 / Chapter II.1 --- Synthesis of racemic planar chiral PPV by bimolecular polymerization using the Horner-Emmons-Wadsworth reaction --- p.14 / Chapter II.2 --- Formation of racemic [n]paracyclophane-based homo-PPVs from rac- bis(chloromethyl)[n]paracyclophanes by the Gilch reaction --- p.17 / Chapter II.3 --- Preparation of enantiopure bis(halomethyl)[n]paracyclophanes to be used as monomers for the synthesis of planar chiral non-racemic PPVs --- p.21 / Chapter II.4 --- Synthesis of [ 14] [ 14]metaparacyclophane ´ؤthe first example of a [m] [n]metaparacyclophane --- p.24 / Chapter II.5 --- Synthesis of enantiopure [n]paracyclophane-based homo-PPVs from enantiopure bis(bromomethyl)[n]paracyclophanes by the Gilch reaction --- p.29 / Chapter II.6 --- "Copolymers formation from enantiopure bis(bromomethyl)[n]paracyclophanes and racemic α,α'-dibromo-2,5-bis(3,7-dimethyloctyloxy)-p-xylene by the Gilch reaction" --- p.32 / Chapter II.7 --- "Characterization of the chiral non-racemic poly[(pR/pS)-[n]-2,5-paracyclo-1,4- phanylene-(E)-vinylene]-co-[2,5-bis(3,7-dimethyloctyloxy)-l,4-phenylene- (E)-vinylene] polymers" --- p.35 / Chapter III --- Conclusion --- p.53 / Chapter IV --- Experimental --- p.54 / References --- p.78 / Spectra --- p.82

*Please refer to dissertation for diagrams. / In addition, a precursor of tetraphenylene-based monodentate ligand ( S,S)-114 was also prepared, and the structures of five compounds, namely 89, 124, 125, 133 and 137 were examined by X-ray crystallographic analysis. These structural determinations were relevant in establishing regiochemistry and absolute stereochemistry.* / In the synthesis of enantiopure (S,R,S)-48 and (R,S,R)-48, two routes were successfully employed. One way was to follow the same pathway for the synthesis of racemic 48 by using enantiopure (S,S)- and (R,R)-1,8,9,16-teramethoxytetraphenylenes [(S,S)-89 and (R,R)- 89] as staring materials. Another way was by direct resolution of racemic 48 via derivatization into its two diastereomeric hexakis-(S)-camphorsulfonates 135 and 136. / In the synthesis of racemic 48, 3-nitrophenol (115) was employed as the starting material which upon a series of standard reactions provided 2,2'-diiodo-1,1'-biphenyl (119). Through sequential lithium-iodine exchange and Cu(II)-mediated oxidative cyclocoupling, 119 was converted to 1,8,9,16-tetramethoxytetraphenylene (89) . The key intermediate 1,8-dihydroxy-9,16-dimethoxytetraphenylene (87) was obtained by partial demethylation of 89. This intermediate was transformed to 1,4,5,8-tetrahydroxy-9,16-dimethoxytetraphenylene (126) by a quinone-hydroquinone strategy. Demethylation of 126 furnished the target compound 48. / This thesis describes the synthesis of 1,4,5,8,9,16-hexahydroxytetraphenylene (48)* in its racemic and enantiopure (S,R,S) and ( R,S,R) forms. Some essential background and previous works in this area are presented in the first chapter. / Wu Anhui. / "August 2006." / Adviser: Henry N. C. Wong. / Source: Dissertation Abstracts International, Volume: 68-03, Section: B, page: 1649. / Thesis (Ph.D.)--Chinese University of Hong Kong, 2006. / Includes bibliographical references (p. 80-85). / Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Electronic reproduction. [Ann Arbor, MI] : ProQuest Information and Learning, [200-] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Abstracts in English and Chinese. / School code: 1307.