Multifunctional Hydrazone‐Based AIEgens Enabled by Hydrogen‐Halogen Interaction

Author:

Zhang Minjie1ORCID,Zhang Jianyu1ORCID,Zhang Zicong2,Kwok Ryan T.K.1,Lam Jacky W. Y.1,Jia Guocheng1,Tang Ben Zhong1234ORCID

Affiliation:

1. Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction The Hong Kong University of Science and Technology Clear Water Bay Kowloon Hong Kong 999077 China

2. School of Science and Engineering Shenzhen Institute of Aggregate Science and Technology The Chinese University of Hong Kong (CUHK‐Shenzhen) Guangdong Shenzhen 518172 China

3. Center for Aggregation‐Induced Emission South China University of Technology Guangzhou 510640 China

4. AIE Institute Guangzhou Development District Huangpu Guangzhou 510530 China

Abstract

AbstractStimuli‐responsive molecules with dynamic covalent bonds show physicochemical changes in response to external stimuli but also exhibit active molecular motions and poor luminescent properties. Hence, the manipulation and balance of dynamic and static behaviors are crucial for the development of multifunctional materials. In this work, a series of hydrazone‐based compounds with aggregation‐induced emission characteristics and hydrogen‐halogen interactions are designed and synthesized. Among them, TPAHPyCl showed the highest quantum yield of 54.0% and morphology‐dependent mechanochromic properties due to the strong chlorine‐hydrogen interactions and other multiple intermolecular interactions in the aggregate state. With the help of the turn‐on emission response to the non‐polar environment of lipid droplets, TPAHPyCl is also utilized for high‐resolution latent fingerprint detection and intracellular lipid‐droplet imaging, demonstrating multiple functions with dynamic and static properties. This work highlights the role of halogen‐hydrogen interactions and provides a new strategy to develop stimuli‐responsive materials with dynamic and static features.

Funder

National Natural Science Foundation of China

Science, Technology and Innovation Commission of Shenzhen Municipality

Innovation and Technology Commission - Hong Kong

Publisher

Wiley

Subject

Atomic and Molecular Physics, and Optics,Electronic, Optical and Magnetic Materials

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