A novel ortho/ bay annulation reaction of perylene bisimide (PBI) has been explored in a single step synthetic procedure using perylene bisimide 1 and 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the absence of any metal catalyst. The single crystal solid-state X-ray diffraction structure showed a distorted framework of DBU-fused PBI 2. Compound 2 exhibited intense near-infrared absorption up to 950 nm. Reversible protonation and deprotonation accompany drastic changes in the photophysical characteristics. Further, the reaction of perylene biscarboxyanhydride with DBU offered a caprolactam ring-substituted perylene bisimide 3.
Diverse applications of rylenediimides
are attributed to the accessibility
of simple methodologies to obtain versatile halogenated precursors.
Terrylene diimides are important molecular platforms to achieve materials
with NIR absorption and emission. In this work, we present a simple
synthesis for the hitherto unknown di- and tribromo-TDIs. Regioisomerically
pure dibromo TDIs, including an elusive 1,14-derivative, could be
successfully isolated and structurally characterized along with tribromo-TDI.
The utility of these bromo derivatives has also been demonstrated
with a redox anchoring.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.