Indexed by:
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 pi-surfaces toward the maximization of shape complementarity. As we demonstrate for helicenes it is indeed possible by pure van-der-Waals interactions (pi-pi interactions and CH-pi interactions) to accomplish enantioselective binding. This is shown for a novel benzo[ghi]perylene trisimide (BPTI) receptor whose pi-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 pi-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 pi-scaffolds of electron-rich [6]helicene and electron-poor BPTI.
Keyword:
Reprint 's Address:
Version:
Source :
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN: 1433-7851
Year: 2022
Issue: 15
Volume: 61
1 6 . 6
JCR@2022
1 6 . 1 0 0
JCR@2023
ESI Discipline: CHEMISTRY;
ESI HC Threshold:74
JCR Journal Grade:1
CAS Journal Grade:1
Cited Count:
WoS CC Cited Count: 18
SCOPUS Cited Count: 19
ESI Highly Cited Papers on the List: 0 Unfold All
WanFang Cited Count:
Chinese Cited Count:
30 Days PV: 2
Affiliated Colleges: