Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 10, Issue 22, Pages 5685-5697Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d3qo01389h
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In this study, a new synthetic strategy was reported to control the structural and fluorescence properties of perylene bisimide (PBI) dyes by employing a 1,12-bay-substitution pattern. Novel perylene dyes with excellent structural and optical properties were successfully obtained through further functionalization of 1,12-dihydroxy-PBI derivatives.
Establishing suitable design strategies to tailor the functional properties of perylene bisimide (PBI) dyes is critical for their successful application in various devices. Herein, we report a new synthetic strategy to tune their structural and fluorescence properties by employing a 1,12-bay-substitution pattern that has been seldomly investigated in the past. Central to the strategy is the use of 1,12-dihydroxy-PBI as a starting compound and the subsequent bridging of these hydroxy bay-functional groups with either a boron, carbon or silicon atom resulting in derivatives with a rigidified perylene core. This is followed by a detailed exploration of synthetic possibilities to functionalize the unsubstituted 6,7-positions at the opposite bay area to achieve novel perylene dyes with excellent structural and optical properties. The fluorescence color could be tuned from green to dark-orange while retaining the almost unity fluorescence quantum yield in solution. Moreover, a strong fluorescence with quantum yields as high as 40% has been observed for powders, which clearly illustrates the potential of the presented structural design to obtain new solid-state emitters. The bridging of 1,12-dihydroxy-PBI with either a boron, carbon or silicon atom and further functionalization yielded novel perylene dyes with excellent tuned optical properties, showing strong fluorescence in solution as well as the in solid-state.
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