Cargando…
Enantioselective Recognition of Helicenes by a Tailored Chiral Benzo[ghi]perylene Trisimide π‐Scaffold
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 fo...
Autores principales: | , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9303377/ https://www.ncbi.nlm.nih.gov/pubmed/35103371 http://dx.doi.org/10.1002/anie.202117625 |
_version_ | 1784751849529671680 |
---|---|
author | Teichmann, Ben Krause, Ana‐Maria Lin, Mei‐Jin Würthner, Frank |
author_facet | Teichmann, Ben Krause, Ana‐Maria Lin, Mei‐Jin Würthner, Frank |
author_sort | Teichmann, Ben |
collection | PubMed |
description | 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(−1) and 550 M(−1), respectively, thereby demonstrating the pronounced enantiodifferentiation by the homochiral π‐scaffold of the BPTI host. The enantioselective recognition is even observable by the naked eye due to a specific exciplex‐type emission originating from the interacting homochiral π‐scaffolds of electron‐rich [6]helicene and electron‐poor BPTI. |
format | Online Article Text |
id | pubmed-9303377 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-93033772022-07-22 Enantioselective Recognition of Helicenes by a Tailored Chiral Benzo[ghi]perylene Trisimide π‐Scaffold Teichmann, Ben Krause, Ana‐Maria Lin, Mei‐Jin Würthner, Frank Angew Chem Int Ed Engl Communications 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(−1) and 550 M(−1), respectively, thereby demonstrating the pronounced enantiodifferentiation by the homochiral π‐scaffold of the BPTI host. The enantioselective recognition is even observable by the naked eye due to a specific exciplex‐type emission originating from the interacting homochiral π‐scaffolds of electron‐rich [6]helicene and electron‐poor BPTI. John Wiley and Sons Inc. 2022-02-18 2022-04-04 /pmc/articles/PMC9303377/ /pubmed/35103371 http://dx.doi.org/10.1002/anie.202117625 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Teichmann, Ben Krause, Ana‐Maria Lin, Mei‐Jin Würthner, Frank Enantioselective Recognition of Helicenes by a Tailored Chiral Benzo[ghi]perylene Trisimide π‐Scaffold |
title | Enantioselective Recognition of Helicenes by a Tailored Chiral Benzo[ghi]perylene Trisimide π‐Scaffold |
title_full | Enantioselective Recognition of Helicenes by a Tailored Chiral Benzo[ghi]perylene Trisimide π‐Scaffold |
title_fullStr | Enantioselective Recognition of Helicenes by a Tailored Chiral Benzo[ghi]perylene Trisimide π‐Scaffold |
title_full_unstemmed | Enantioselective Recognition of Helicenes by a Tailored Chiral Benzo[ghi]perylene Trisimide π‐Scaffold |
title_short | Enantioselective Recognition of Helicenes by a Tailored Chiral Benzo[ghi]perylene Trisimide π‐Scaffold |
title_sort | enantioselective recognition of helicenes by a tailored chiral benzo[ghi]perylene trisimide π‐scaffold |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9303377/ https://www.ncbi.nlm.nih.gov/pubmed/35103371 http://dx.doi.org/10.1002/anie.202117625 |
work_keys_str_mv | AT teichmannben enantioselectiverecognitionofhelicenesbyatailoredchiralbenzoghiperylenetrisimidepscaffold AT krauseanamaria enantioselectiverecognitionofhelicenesbyatailoredchiralbenzoghiperylenetrisimidepscaffold AT linmeijin enantioselectiverecognitionofhelicenesbyatailoredchiralbenzoghiperylenetrisimidepscaffold AT wurthnerfrank enantioselectiverecognitionofhelicenesbyatailoredchiralbenzoghiperylenetrisimidepscaffold |