Enantioselective Light Harvesting with Perylenediimide Guests on Self‐Assembled Chiral Naphthalenediimide Nanofibers

Abstract

Self-assembling molecular systems often display amplified chirality compared to the monomeric state, which makes the molecular recognition more sensitive to chiral analytes. Herein, we report the almost absolute enantioselective recognition of a chiral perylenediimide (PDI) molecule by chiral supramolecular nanofibers of a bichromophoric naphthalenediimide (NDI) derivative. The chiral recognition was evaluated through the Förster resonance energy transfer (FRET) from the NDI-based host nanofibers to the guest PDI molecules. The excitation energy was successfully transferred to the guest molecule through efficient energy migration along the host nanofiber, thus demonstrating the light-harvesting capability of these hybrid systems. Furthermore, circularly polarized luminescence (CPL) was enantioselectively sensitized by the guest molecule as the wavelength band and sign of the CPL signal were switched in response to the chiral guest molecule.

Recent Progress on Circularly Polarized Luminescent Materials for Organic Optoelectronic Devices

“…Additionally, the formation of the ordered chiral nanomaterials resulted in a significant enhancement in the intensity of CPL signals due to the occurrence of chirality transfer from chiral center to perylene moiety. Furthermore, the study was extended using a series of bichromophoric perylenediimide derivatives ( 203 – 205 ) . The results showed that the intensity of CPL signals strongly depended on the self‐assembled states of the molecules, and efficient modulation of bichromophoric systems contributed to the formation of highly ordered aggregation state through intermolecular interactions which is conducive to the enhanced CPL.…”

Covalently Linked Perylene Diimide–Polydiacetylene Nanofibers Display Enhanced Stability and Photocurrent with Reversible FRET Phenomenon

“…Owing to their intriguing structural, optical, and electrical properties, perylene diimde (PDI) derivatives have been extensively investigated for use in a variety of systems including functional supramolecules, organic solar cells, organic field‐effect transistors (OFETs), and sensors . Because they undergo facile self‐assembly as a consequence of favorable π–π stacking, hydrogen bonding, and van der Waals interactions, certain PDI derivatives form well‐defined 1D nanostructures such as nanofibers and nanotubes . However, although these 1D PDI nanostructures serve as key components in optoelectronic devices, they often suffer from poor stability.…”

Visualization of Stereoselective Supramolecular Polymers by Chirality‐Controlled Energy Transfer

“…Although, various molecular designs have been reported to modulate the energy‐transfer process in supramolecular assemblies, a chirality‐based approach to control energy transfer has been seldom reported . During the review of this manuscript, Kawai and co‐workers reported enantioselective light harvesting and CPL …”