ArticleJournal of the American Chemical Society2022
The Pink Box: Exclusive Homochiral Aromatic Stacking in a Bis-perylene Diimide Macrocycle.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- A Mechanical Planar Chiral Rotaxane Induces Single-Handed Helicity in a Twisted Perylene Diimide.Angewandte Chemie (International ed. in English) · 2026Article
- Delicate molecular design, self-assembly and functional applications of chiral cyclophanes.Chemical science · 2026Review
- Conformational switching modulates excited-state pathways in a cofacial perylene dimer.Chemical science · 2026Article
- Chirally locked and dynamic bis-perylene diimide macrocycles with multiple sources of chirality.Communications chemistry · 2026Article
- Circular Dichroism and Multiphoton Circularly Polarized Luminescence Switching Using a Bis-perylene Diimide Macrocycle.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Rationalising Exciton Interactions in Aggregates Based on the Transition Density.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Core-Twisted, Cationic Perylene Diimides; Homochiral Dimerization and Chiroptical Anion Sensing.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- A Bis-Perylene Diimide Macrocycle Chiroptical Switch.Angewandte Chemie (International ed. in English) · 2025Article
- Intermolecular Anionic Mixed-Valence and π-Dimer Complexes of ortho-Pentannulated Bisazacoronene Diimide.Angewandte Chemie (International ed. in English) · 2025Article
- Boosting the circularly polarized luminescence of pyrene-tiaraed pillararenes through mechanically locking.Nature communications · 2024Article
- Dual-mode electrochemical and electrochemiluminescence detection of dopamine based on perylene diimide self-assembly material.Mikrochimica acta · 2024Article
- Investigating the diastereoselective synthesis of a macrocycle under Curtin-Hammett control.Chemical science · 2024Article
- A Chirally Locked Bis-perylene Diimide Macrocycle: Consequences for Chiral Self-Assembly and Circularly Polarized Luminescence.Journal of the American Chemical Society · 2024Article
- Preferential molecular recognition of heterochiral guests within a cyclophane receptor.Nature communications · 2023Article
- Circularly polarised luminescence from excimer emission of anthracene derivatives complexed with γ-cyclodextrin in the solid state.RSC advances · 2023Article
- Naphthalimide-based conjugated macrocycles possessing tunable self-assembly and supramolecular binding behaviours.Frontiers in chemistry · 2022Article
Corrections and comments
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Authors and funding
8 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
This work showcases chiral complementarity in aromatic stacking interactions as an effective tool to optimize the chiroptical and electrochemical properties of perylene diimides (PDIs). PDIs are a notable class of robust dye molecules and their rich photo- and electrochemistry and potential chirality make them ideal organic building blocks for chiral optoelectronic materials. By exploiting the new bay connectivity of twisted PDIs, a dynamic bis-PDI macrocycle (the "Pink Box") is realized in which homochiral PDI-PDI π-π stacking interactions are switched on exclusively. Using a range of experimental and computational techniques, we uncover three important implications of the macrocycle's chiral complementarity for PDI optoelectronics. First, the homochiral intramolecular π-π interactions anchor the twisted PDI units, yielding enantiomers with half-lives extended over 400-fold, from minutes to days (in solution) or years (in the solid state). Second, homochiral H-type aggregation affords the macrocycle red-shifted circularly polarized luminescence and one of the highest dissymmetry factors of any small organic molecule in solution (
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.