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Observation of Chiral-selective room-temperature phosphorescence enhancement via chirality-dependent energy transfer.

ABSTRACT: Pure organic room-temperature phosphorescence (RTP), particularly from guest-host doped systems, has seen exponential growth in the last several years due to their high modulation flexibility, and yet challenges remain with respect to mechanistic elucidations and advantageous applications. Here we show that by constructing guest-host doped RTP systems from chiral components, namely, chiral amino compound-modified phthalimide hosts and naphthalimide guests, a chiral-selective RTP enhancement phenomenon can be observed. For example, R-enantiomeric guests in R-enantiomeric hosts produce strong red RTP afterglow while no appreciable RTP could be observed in the S-R guest-host counterpart. An unprecedented RTP intensity difference > 10² folds with the ability to distinguish an enantiomeric excess of 98% could be achieved. Temperature-dependent measurements suggest that a chirality-dependent energy transfer process may be involved in the observed phenomenon, which can be harnessed to extend the RTP application to the chiral recognition of amino compounds, such as amino alcohols.

SUBMITTER: Chen B

PROVIDER: S-EPMC10024683 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature

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Observation of Chiral-selective room-temperature phosphorescence enhancement via chirality-dependent energy transfer.

Chen Biao B Huang Wenhuan W Zhang Guoqing G

Nature communications 20230318 1

Pure organic room-temperature phosphorescence (RTP), particularly from guest-host doped systems, has seen exponential growth in the last several years due to their high modulation flexibility, and yet challenges remain with respect to mechanistic elucidations and advantageous applications. Here we show that by constructing guest-host doped RTP systems from chiral components, namely, chiral amino compound-modified phthalimide hosts and naphthalimide guests, a chiral-selective RTP enhancement phen ...[more]

PMID: 36934094

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Project description:Engineering the electronic excited state manifolds of organic molecules can give rise to various functional outcomes, including ambient triplet harvesting, that has received prodigious attention in the recent past. Herein, we introduce a modular, non-covalent approach to bias the entire excited state landscape of an organic molecule using tunable 'through-space charge-transfer' interactions with appropriate donors. Although charge-transfer (CT) donor-acceptor complexes have been extensively explored as functional and supramolecular motifs in the realm of soft organic materials, they could not imprint their potentiality in the field of luminescent materials, and it still remains as a challenge. Thus, in the present study, we investigate the modulation of the excited state emission characteristics of a simple pyromellitic diimide derivative on complexation with appropriate donor molecules of varying electronic characteristics to demonstrate the selective harvesting of emission from its locally excited (LE) and CT singlet and triplet states. Remarkably, co-crystallization of the pyromellitic diimide with heavy-atom substituted and electron-rich aromatic donors leads to an unprecedented ambient CT phosphorescence with impressive efficiency and notable lifetime. Further, gradual minimizing of the electron-donating strength of the donors from 1,4-diiodo-2,3,5,6-tetramethylbenzene (or 1,2-diiodo-3,4,5,6-tetramethylbenzene) to 1,2-diiodo-4,5-dimethylbenzene and 1-bromo-4-iodobenzene modulates the source of ambient phosphorescence emission from the 3CT excited state to 3LE excited state. Through comprehensive spectroscopic, theoretical studies, and single-crystal analyses, we elucidate the unparalleled role of intermolecular donor-acceptor interactions to toggle between the emissive excited states and stabilize the triplet excitons. We envisage that the present study will be able to provide new and innovative dimensions to the existing molecular designs employed for triplet harvesting.

Dataset Information

Observation of Chiral-selective room-temperature phosphorescence enhancement via chirality-dependent energy transfer.

Publications

Observation of Chiral-selective room-temperature phosphorescence enhancement via chirality-dependent energy transfer.

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