Excited‐State Intramolecular Proton Transfer Parent Core Engineering for Six‐Level System Lasing Toward 900 nm

Organic molecules which can undergo excited‐state intramolecular proton transfer (ESIPT) process have been considered as ideal gain materials for near‐infrared organic lasers owing to their effective four‐level systems. However, extending lasing wavelength beyond 800 nm with present ESIPT‐active gai...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2022-11, Vol.61 (48), p.e202210422-n/a
Main Authors: Yan, Chang‐Cun, Liu, Yan‐Ping, Yang, Wan‐Ying, Wu, Jun‐Jie, Wang, Xue‐Dong, Liao, Liang‐Sheng
Format: Article
Language:English
Subjects:
Excited-State Intramolecular Proton Transfer
Infrared lasers
Lasers
Lasing
Molecular Design
Near-Infrared Emission
Organic chemistry
Organic lasers
Organic Solid-State Laser
Protons
Six-Level System
System effectiveness
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Summary:Organic molecules which can undergo excited‐state intramolecular proton transfer (ESIPT) process have been considered as ideal gain materials for near‐infrared organic lasers owing to their effective four‐level systems. However, extending lasing wavelength beyond 800 nm with present ESIPT‐active gain materials is still in challenge. Herein, we established a molecular design strategy that operates via extending the π‐conjugated system of the ESIPT parent core to enhance the cascaded double ESIPT process and thus to achieve the red‐shifted six‐level system lasing. Concretely, a model molecule with 1,9‐dihydroxyanthracene as the ESIPT parent core was designed and synthesized, which was proved to undergo twice cascaded ESIPT processes while the 1,8‐dihydroxynaphthalene‐based analogue can only undergo once ESIPT process based on DFT calculations and ultrafast dynamics analyses. Finally, a six‐level system lasing toward 900 nm was achieved with a low threshold of 27.4 μJ cm−2. A six‐level system lasing toward 900 nm was achieved with a low lasing threshold of 27.4 μJ cm−2 through engineering of the excited‐state intramolecular proton transfer (ESIPT) of the parent core. This work demonstrates that extending the π‐conjugated system of the ESIPT parent core can effectively enhance the second proton transfer process in a cascaded double ESIPT system.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202210422