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author:

Teichmann, Ben (Teichmann, Ben.) [1] | Krause, Ana-Maria (Krause, Ana-Maria.) [2] | Lin, Mei-Jin (Lin, Mei-Jin.) [3] (Scholars:林梅金) | Wuerthner, Frank (Wuerthner, Frank.) [4]

Indexed by:

EI SCIE

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:

Binding Studies Chirality Dyes Enantioselectivity Molecular Recognition Pigments

Community:

  • [ 1 ] [Teichmann, Ben]Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
  • [ 2 ] [Krause, Ana-Maria]Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
  • [ 3 ] [Wuerthner, Frank]Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
  • [ 4 ] [Teichmann, Ben]Univ Wurzburg, Ctr Nanosyst Chem, D-97074 Wurzburg, Germany
  • [ 5 ] [Krause, Ana-Maria]Univ Wurzburg, Ctr Nanosyst Chem, D-97074 Wurzburg, Germany
  • [ 6 ] [Wuerthner, Frank]Univ Wurzburg, Ctr Nanosyst Chem, D-97074 Wurzburg, Germany
  • [ 7 ] [Teichmann, Ben]Fuzhou Univ, Coll Chem, State Key Lab Photocatalysis Energy & Environm, Fuzhou 350116, Peoples R China
  • [ 8 ] [Lin, Mei-Jin]Fuzhou Univ, Coll Chem, State Key Lab Photocatalysis Energy & Environm, Fuzhou 350116, Peoples R China

Reprint 's Address:

  • 林梅金

    [Wuerthner, Frank]Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany;;[Wuerthner, Frank]Univ Wurzburg, Ctr Nanosyst Chem, D-97074 Wurzburg, Germany;;[Lin, Mei-Jin]Fuzhou Univ, Coll Chem, State Key Lab Photocatalysis Energy & Environm, Fuzhou 350116, Peoples R China

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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: 1

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