| Abstract
| - This paper concerns the synthesis of 1,16-dihydroxytetraphenylene (DHTP) (2) by employing anovel NBS bromination route. (±)-DHTP 2 was successfully resolved into its optical antipodes andconverted to (±)-1,16-bis(diphenylphosphino)tetraphenylene (BPTP) (26), whose platinum complexBPTP−PtCl2 (27) was also obtained. As a hydrogen bond donor, racemic and optically active DHTP2 was allowed to assemble with 4,4‘-bipyridine to form single crystals of good quality. X-rayDiffraction studies of these crystals revealed that the crystallographic packing of the hydrogenbonded complex between (±)-2 and 4,4‘-bipyridine was different from the one formed from (S)-2and 4,4‘-bipyridine. It was found that an infinite zigzag chain with alternate chirality was formedin the assembly of (±)-2 and 4,4‘-bipyridine, while (S)-2 and 4,4‘-bipyridine failed to show the sameassembly pattern. The reason (±)-2 formed an alternate and zigzag chain with 4,4‘-bipyridine wasmost likely due to the inherent stability of this supramolecular assembly. The chiral recognitionbetween 2 and optically active BINAP under the direction of platinum(II) has also been examined.1H and 31P NMR spectroscopic studies demonstrated that there was an obvious discrimination of2 between the enantiomers of BINAP−PtCO3.
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