ArticleAngewandte Chemie (International ed. in English)2022
Enantioselective Recognition of Helicenes by a Tailored Chiral Benzo[ghi]perylene Trisimide π-Scaffold.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 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
- Stereoselective synthesis of E-shaped double helicene analogues via organocatalytic intermolecular cycloaddition.Nature communications · 2026Article
- Skeletal rearrangement of [4]helicenes under acidic conditions: dynamic chirality and improved properties by subsequent peripheral editing.Chemical science · 2026Article
- Dynamics and Conformational Stability of Chiral Bay-Phenolate-Substituted Twisted Octaazaperopyrenedioxides (OAPPDOs).Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Catalytic kinetic resolution of helical polycyclic phenols via an organocatalyzed enantioselective dearomative amination reaction.Science advances · 2024Article
- Enantioselective synthesis of [4]helicenes by organocatalyzed intermolecular C-H amination.Nature communications · 2024Article
- Preferential molecular recognition of heterochiral guests within a cyclophane receptor.Nature communications · 2023Article
- Chemo- and Regioselective Multiple C(spAngewandte Chemie (International ed. in English) · 2022Article
- Enantioselective Recognition of Helicenes by a Tailored Chiral Benzo[ghi]perylene Trisimide π-Scaffold.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
4 authors.
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Abstract
Enantioselective molecular recognition of chiral molecules that lack specific interaction sites for hydrogen bonding or Lewis acid-base interactions remains challenging. Here we introduce the concept of tailored chiral π-surfaces toward the maximization of shape complementarity. As we demonstrate for helicenes it is indeed possible by pure van-der-Waals interactions (π-π interactions and CH-π interactions) to accomplish enantioselective binding. This is shown for a novel benzo[ghi]perylene trisimide (BPTI) receptor whose π-scaffold is contorted into a chiral plane by functionalization with 1,1'-bi-2-naphthol (BINOL). Complexation experiments of enantiopure (P)-BPTI with (P)- and (M)-[6]helicene afforded binding constants of 10 700 M
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