Visualization of Stereoselective Supramolecular Polymers by Chirality‐Controlled Energy Transfer

Abstract

Chirality-driven self-sorting is envisaged to efficiently control functional properties in supramolecular materials.H owever,t he challenge arises because of al acko f analytical methods to directly monitor the enantioselectivity of the resulting supramolecular assemblies.P resented herein are two fluorescent core-substituted naphthalene-diimidebased donor and acceptor molecules with minimal structural mismatcha nd they comprise strong self-recognizing chiral motifs to determine the self-sorting process.Asaconsequence, stereoselective supramolecular polymerization with an unprecedented chirality control over energy transfer has been achieved. This chirality-controlled energy transfer has been further exploited as an efficient probe to visualize microscopically the chirality driven self-sorting.

A de novo strategy for predictive crystal engineering to tune excitonic coupling

“…4c). Whereas in 8A and 9A the short-lived component dominated the emission, in 15 A, the long-lived PL 47 became the more prominent component. This observation is consistent with the larger rotation angle θ , which would lead to a loss of the cofacial packing.…”

Bicomponent Fluorescent System Composed of Peptide-Substituted Naphthalenediimide and Carbon Dots as Nanothermometer

“…Naphthalene dianhydride (NDA) is one of the important π-conjugated organic molecules among the rylene dyes . The endowed physical properties including molecular planarity, air stability, chemical robustness, and high π-acidity make NDA a promising candidate in diverse research fields like organic light-emitting diodes (OLED), photovoltaic devices, solar cells, field effect transistors, bioprobes, and others. − Functionalization with the peptides at the periphery of NDA leads to the formation of peptide-appended imide and core-substituted naphthalenediimides (NDIs and c-NDIs). − The incorporation of a peptide may facilitate tuning of the self-assembling property of NDIs using the H-bonding interactions of the CO-NH group of the peptide. − Depending on the electron-donating capability of a functional group at the core position of NDIs, a rainbow collection of fluorescent c-NDI can be obtained . The c-NDIs possess high fluorescence quantum yield and cover the absorption span over the entire visible range .…”

Steering Triplet–Triplet Annihilation Upconversion through Enantioselective Self-Assembly in a Supramolecular Gel

“…Great efforts to mimic such chiral selection processes have led to the development of artifical supramolecular systems, with a high level of chiral selection ability. − Also, attempts to mimic natural light-harvesting systems have driven the fabrication of multichromophoric assemblies with an ordered organization of donor–acceptor units. − However, energy transfer and chirality selection processes in artificial supramolecular systems have mostly been reported separately. Only limited efforts have focused on the fabrication of supramolecular sysems integrating chiral selection with an energy transfer process. − In 2017, Kawai, Nakashima, and co-workers presented an elegant example of almost absolutely enanotiselective light-harvesting behavior and circularly polarized luminescence (CPL) on self-assembled donor–acceptor nanofibers, in which the supramolecular nanofibers of an R -chiral bichromophoric naphthalenediimide derivative can selectively sensitize the S -chiral perylenediimide guest molecule through a Förster resonance energy tansfer (FRET) mechanism . However, such a sensitization ability was absent when it was paired with the opposite R -chiral guest molecule.…”

“…Almost at the same time, the George group also reported a chirality-controlled energy transfer based on the FRET mechanism in core-substituted chiral naphthalene diimide derivatives bearing different substituent groups as energy donors and acceptors. 29 Very interestingly, the chirality-driven self-sorting supramolecular assembly and the selective energy transfer process can be visualied microscopically. So far, reports on chirality-controlled energy transfer are still rare.…”