Year: 2024
Type: article
Abstract: This work reports the synthesis and self‐assembly of perylene diimide (PDI)‐containing macrocycles designed for facile and high‐throughput production of shape‐persistent, macrocyclic organic electronic materials. Specifically, utilizing dynamic covalent chemistry (DCvC), this work showcases ditopic thiols can be utilized as building blocks toward 3D materials with defined porosity, low‐lying unoccupied molecular orbitals, and intrinsic fluorescence. The PDI disulfide‐linked macrocycles are generated in a single step from the thiolic building block to yield dimeric through pentameric assemblies in overall 95% combined yield; moreover, following self‐assembly, the disulfide ensemble is sulfur extruded to the more kinetically stable thioether in 79% combined yield. The modular design suggests these methods can be used to easily self‐assemble other electronically active precursors for utility in porous macrocyclic materials where stepwise pathways may be laborious and/or low yielding.
Source: Advanced Functional Materials
Institution: University of Oregon
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
Awards: Dynamic covalent self-assembly and self-sorting of 2-dimensional and 3-dimensional nanohoops and cages, G3871319019, MRI: Acquisition of a High Resolution Mass Spectrometer for Research and Education at a University of Oregon Facility, G7118409798, NRT-URoL: Molecular Probes and Sensors for Complex Environments
OpenAlex ID: W4393856636