Abstract
Two azo-perylene derivatives (PBI-AZO-1 and PBI-AZO-2) with two alkyl chains and six alkoxy chains were designed and synthesized in yield of 63% and 49%, respectively. PBI-AZO-1 showed no mesophase but PBI-AZO-2 exhibited ordered hexagonal columnar mesophase based on the favorable effects of multiple alkyl chains. PBI-AZO-1 and PBI-AZO-2 exhibited the cis and trans azo-isomerization under radiation of UV light and the fluorescence quantum yields enhanced remarkably from 0.61 and 0.64 to 0.78 and 0.88, respectively. The ordered hexagonal columnar mesophase of PBI-AZO-2 was destroyed by isomerization due to the influence of asymmetrical mixture of cis and trans isomers. The transformation of liquid crystal/non-liquid crystal of PBI-AZO-2 before and after cis/trans isomerization displayed good reversibility by storing the sample for 15 days at room temperature. This kind of liquid crystallic behavior tuned by azo isomerization was first observed for perylene liquid crystal.
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