Intramolecular Energy and Solvent‐Dependent Chirality Transfer within a BINOL‐Perylene Hetero‐Cyclophane

Abstract: Multichromophoric macrocycles and cyclophanes are important supramolecular architectures for the elucidation of interchromophoric interactions originating from precise spatial organization. Herein, by combining an axially chiral binaphthol bisimide (BBI) and a bay‐substituted conformationally labile twisted perylene bisimide (PBI) within a cyclophane of well‐defined geometry, we report a chiral PBI hetero‐cyclophane (BBI‐PBI) that shows intramolecular energy and solvent‐regulated chirality transfer from the BBI to the PBI subunit. Excellent spectral overlap and spatial arrangement of BBI and PBI lead to efficient excitation energy transfer and subsequent PBI emission with high quantum yield (80–98 %) in various solvents. In contrast, chirality transfer is strongly dependent on the respective solvent as revealed by circular dichroism (CD) spectroscopy. The combination of energy and chirality transfer affords a bright red circularly polarized luminescence (CPL) from the PBI chromophore by excitation of BBI.

Standort
Deutsche Nationalbibliothek Frankfurt am Main
Umfang
Online-Ressource
Sprache
Englisch

Erschienen in
Intramolecular Energy and Solvent‐Dependent Chirality Transfer within a BINOL‐Perylene Hetero‐Cyclophane ; day:21 ; month:06 ; year:2022 ; extent:1
Angewandte Chemie / International edition. International edition ; (21.06.2022) (gesamt 1)

Urheber
Ouyang, Guanghui
Rühe, Jessica
Zhang, Yang
Lin, Mei‐Jin
Liu, Minghua
Würthner, Frank

DOI
10.1002/anie.202206706
URN
urn:nbn:de:101:1-2022062215032180776458
Rechteinformation
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Letzte Aktualisierung
15.08.2025, 07:29 MESZ

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Beteiligte

  • Ouyang, Guanghui
  • Rühe, Jessica
  • Zhang, Yang
  • Lin, Mei‐Jin
  • Liu, Minghua
  • Würthner, Frank

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