ESIPT-Inspired Dual-Mode Photoswitches with Fast Molecular Isomerization in the Solid State

Yahui Chen; You Rim Lee; Wenjing Wang; Yu Fang; Sheng Lu; Jingjing Han; Xiaoqiang Chen; Myung Hwa Kim; Juyoung Yoon

doi:10.1002/anie.202301765

ESIPT-Inspired Dual-Mode Photoswitches with Fast Molecular Isomerization in the Solid State

Yahui Chen, You Rim Lee, Wenjing Wang, Yu Fang, Sheng Lu, Jingjing Han, Xiaoqiang Chen, Myung Hwa Kim, Juyoung Yoon

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

39 Scopus citations

Abstract

Photoswitchable materials have attracted considerable attention in various fields. Developing excellent solid-state dual-mode photoswitches is an important but challenging task. Herein, we propose a new strategy to construct an excited-state intramolecular proton transfer (ESIPT) inspired photoswitch (DiAH-pht) that possesses aggregation-induced emission (AIE) features and displays a fast molecular isomerization process characterized by dual-mode behavior in the solid state. Mechanistic studies indicate that introduction of a bulky group can create a folded molecular conformation that provides adequate volume to facilitate photoisomerization and the enhanced ESIPT effect can boost the isomerization process. The feasibility of our strategy was further demonstrated by the activated photoisomerization performance of the Schiff base derivatives. Furthermore, DiAH-pht shows good performance in the fields of dual-mode information encryption and high-density data storage.

Original language	English
Article number	e202301765
Journal	Angewandte Chemie - International Edition
Volume	62
Issue number	15
DOIs	https://doi.org/10.1002/anie.202301765
State	Published - 3 Apr 2023

Bibliographical note

Funding Information:
This work was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF‐2018R1A6A1A03025340) and the Korea government (MSIT) (2022R1A2C3005420 for J.Y.). The work was also supported financially by the National Natural Science Foundation of China (21978131). We thank Materials Characterization Center of East China Normal University for help with the measurement of femtosecond transient absorption spectra. The measurements of XRD and NMR were performed using the single‐crystal X‐ray diffractometer and NMR 300 MHz at the National Research Facilities and Equipment Center (NanoBioEnergy Materials Center) at Ewha Womans University.

Funding Information:
This work was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF-2018R1A6A1A03025340) and the Korea government (MSIT) (2022R1A2C3005420 for J.Y.). The work was also supported financially by the National Natural Science Foundation of China (21978131). We thank Materials Characterization Center of East China Normal University for help with the measurement of femtosecond transient absorption spectra. The measurements of XRD and NMR were performed using the single-crystal X-ray diffractometer and NMR 300 MHz at the National Research Facilities and Equipment Center (NanoBioEnergy Materials Center) at Ewha Womans University.

Publisher Copyright:
© 2023 Wiley-VCH GmbH.

Keywords

Aggregation-Induced Emission
Dual-Mode
Excited-State Intramolecular Proton Transfer
Information Encryption
Solid-State Photoswitches

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title = "ESIPT-Inspired Dual-Mode Photoswitches with Fast Molecular Isomerization in the Solid State",

abstract = "Photoswitchable materials have attracted considerable attention in various fields. Developing excellent solid-state dual-mode photoswitches is an important but challenging task. Herein, we propose a new strategy to construct an excited-state intramolecular proton transfer (ESIPT) inspired photoswitch (DiAH-pht) that possesses aggregation-induced emission (AIE) features and displays a fast molecular isomerization process characterized by dual-mode behavior in the solid state. Mechanistic studies indicate that introduction of a bulky group can create a folded molecular conformation that provides adequate volume to facilitate photoisomerization and the enhanced ESIPT effect can boost the isomerization process. The feasibility of our strategy was further demonstrated by the activated photoisomerization performance of the Schiff base derivatives. Furthermore, DiAH-pht shows good performance in the fields of dual-mode information encryption and high-density data storage.",

keywords = "Aggregation-Induced Emission, Dual-Mode, Excited-State Intramolecular Proton Transfer, Information Encryption, Solid-State Photoswitches",

author = "Yahui Chen and Lee, {You Rim} and Wenjing Wang and Yu Fang and Sheng Lu and Jingjing Han and Xiaoqiang Chen and Kim, {Myung Hwa} and Juyoung Yoon",

note = "Funding Information: This work was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF‐2018R1A6A1A03025340) and the Korea government (MSIT) (2022R1A2C3005420 for J.Y.). The work was also supported financially by the National Natural Science Foundation of China (21978131). We thank Materials Characterization Center of East China Normal University for help with the measurement of femtosecond transient absorption spectra. The measurements of XRD and NMR were performed using the single‐crystal X‐ray diffractometer and NMR 300 MHz at the National Research Facilities and Equipment Center (NanoBioEnergy Materials Center) at Ewha Womans University. Funding Information: This work was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF-2018R1A6A1A03025340) and the Korea government (MSIT) (2022R1A2C3005420 for J.Y.). The work was also supported financially by the National Natural Science Foundation of China (21978131). We thank Materials Characterization Center of East China Normal University for help with the measurement of femtosecond transient absorption spectra. The measurements of XRD and NMR were performed using the single-crystal X-ray diffractometer and NMR 300 MHz at the National Research Facilities and Equipment Center (NanoBioEnergy Materials Center) at Ewha Womans University. Publisher Copyright: {\textcopyright} 2023 Wiley-VCH GmbH.",

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AU - Chen, Yahui

AU - Lee, You Rim

AU - Wang, Wenjing

AU - Fang, Yu

AU - Lu, Sheng

AU - Han, Jingjing

AU - Chen, Xiaoqiang

AU - Kim, Myung Hwa

AU - Yoon, Juyoung

N1 - Funding Information: This work was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF‐2018R1A6A1A03025340) and the Korea government (MSIT) (2022R1A2C3005420 for J.Y.). The work was also supported financially by the National Natural Science Foundation of China (21978131). We thank Materials Characterization Center of East China Normal University for help with the measurement of femtosecond transient absorption spectra. The measurements of XRD and NMR were performed using the single‐crystal X‐ray diffractometer and NMR 300 MHz at the National Research Facilities and Equipment Center (NanoBioEnergy Materials Center) at Ewha Womans University. Funding Information: This work was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF-2018R1A6A1A03025340) and the Korea government (MSIT) (2022R1A2C3005420 for J.Y.). The work was also supported financially by the National Natural Science Foundation of China (21978131). We thank Materials Characterization Center of East China Normal University for help with the measurement of femtosecond transient absorption spectra. The measurements of XRD and NMR were performed using the single-crystal X-ray diffractometer and NMR 300 MHz at the National Research Facilities and Equipment Center (NanoBioEnergy Materials Center) at Ewha Womans University. Publisher Copyright: © 2023 Wiley-VCH GmbH.

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N2 - Photoswitchable materials have attracted considerable attention in various fields. Developing excellent solid-state dual-mode photoswitches is an important but challenging task. Herein, we propose a new strategy to construct an excited-state intramolecular proton transfer (ESIPT) inspired photoswitch (DiAH-pht) that possesses aggregation-induced emission (AIE) features and displays a fast molecular isomerization process characterized by dual-mode behavior in the solid state. Mechanistic studies indicate that introduction of a bulky group can create a folded molecular conformation that provides adequate volume to facilitate photoisomerization and the enhanced ESIPT effect can boost the isomerization process. The feasibility of our strategy was further demonstrated by the activated photoisomerization performance of the Schiff base derivatives. Furthermore, DiAH-pht shows good performance in the fields of dual-mode information encryption and high-density data storage.

AB - Photoswitchable materials have attracted considerable attention in various fields. Developing excellent solid-state dual-mode photoswitches is an important but challenging task. Herein, we propose a new strategy to construct an excited-state intramolecular proton transfer (ESIPT) inspired photoswitch (DiAH-pht) that possesses aggregation-induced emission (AIE) features and displays a fast molecular isomerization process characterized by dual-mode behavior in the solid state. Mechanistic studies indicate that introduction of a bulky group can create a folded molecular conformation that provides adequate volume to facilitate photoisomerization and the enhanced ESIPT effect can boost the isomerization process. The feasibility of our strategy was further demonstrated by the activated photoisomerization performance of the Schiff base derivatives. Furthermore, DiAH-pht shows good performance in the fields of dual-mode information encryption and high-density data storage.

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M3 - Article

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VL - 62

JO - Angewandte Chemie - International Edition

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M1 - e202301765

ER -

ESIPT-Inspired Dual-Mode Photoswitches with Fast Molecular Isomerization in the Solid State

Abstract

Bibliographical note

Keywords

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