Journal Article

PUBDB-2024-06121

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png The Delayed Box: Biphenyl Bisimide Cyclophane, a Supramolecular Nano-environment for the Efficient Generation of Delayed Fluorescence

Garain, S. ; Shoyama, K.Extern* ; Ginder, L.-M. ; Sárosi, M. ; Wuerthner, F. (Corresponding author)Extern*

2024
ACS Publications Washington, DC

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Please use a persistent id in citations: doi:10.1021/jacs.4c07730  doi:10.3204/PUBDB-2024-06121

Abstract: Activating delayed fluorescence emission in a dilute solution via a non-covalent approach is a formidable challenge. In this report, we propose a strategy for efficient delayed fluorescence generation in dilute solution using a non-covalent approach via supramolecularly engineered cyclophane-based nanoenvironments that provide sufficient binding strength to π-conjugated guests and that can stabilize triplet excitons by reducing vibrational dissipation and lowering the singlet–triplet energy gap for efficient delayed fluorescence emission. Toward this goal, a novel biphenyl bisimide-derived cyclophane is introduced as an electron-deficient and efficient triplet-generating host. Upon encapsulation of various carbazole-derived guests inside the nanocavity of this cyclophane, emissive charge transfer (CT) states close to the triplet energy level of the biphenyl bisimide are generated. The experimental results of host–guest studies manifest high association constants up to 10$^4$ M$^{–1}$ as the prerequisite for inclusion complex formation, the generation of emissive CT states, and triplet-state stabilization in a diluted solution state. By means of different carbazole guest molecules, we could realize tunable delayed fluorescence emission in this carbazole-encapsulated biphenyl bisimide cyclophane in methylcyclohexane/carbon tetrachloride solutions with a quantum yield (QY) of up to 15.6%. Crystal structure analyses and solid-state photophysical studies validate the conclusions from our solution studies and provide insights into the delayed fluorescence emission mechanism.

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Contributing Institute(s):

1. DOOR-User (DOOR ; HAS-User)

Research Program(s):

1. 6G3 - PETRA III (DESY) (POF4-6G3) (POF4-6G3)
2. FS-Proposal: I-20230262 (I-20230262) (I-20230262)

Experiment(s):

1. PETRA Beamline P11 (PETRA III)

Appears in the scientific report 2024

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