Aggregation Induced Transition by Modulation of Substituent Groups on Rofecoxib Analogues and Multi‐Stimulus Response Properties

Author:

Chen Nannan1,Wei Yongbo12,Liu Wei13,Wu Tong1,Zhou Jingming1,Ye Yuqiu1,Wang Zexin12,Ke Yanbing13,Jiang Hong13,Xie Lijun13ORCID

Affiliation:

1. Fujian Provincial Key Laboratory of Screening for Novel Microbial Products Fujian Institute of Microbiology Fuzhou Fujian 350007 PR China

2. Department of Medicinal Chemistry, School of Pharmaceutical Engineering Shenyang Pharmaceutical University Shenyang Liaoning 110016 PR China

3. The School of Pharmacy Fujian Medical University Fuzhou Fujian 350122 P.R. China

Abstract

AbstractAggregation‐induced emission luminogens (AIEgens) have been widely investigated due to their promising applications in data storage, organic light‐emitting diodes, and deep tissue bioimaging as compared to conventional fluorophores. In this work, we have designed and synthesized two novel rofecoxib analogues functionalized with different terminal groups (−NH2, −Br) on the benzene ring B. Interestingly, the compound 2 a‐3 with −NH2 substituent shows aggregation‐caused quenching effect whereas the compound 1 b‐3 with −Br group displays aggregation‐induced emission (AIE) property which may be caused by the twisted conformation and restricted – stacking of 1 b‐3 according to the X‐ray single crystal diffraction analysis. These opposite results indicated that the terminal groups could have great influence on the photophysical properties of targets. Moreover, the compound 1 b‐3 exhibited multi‐stimuli response luminescence behaviors under various external stimuli including solvatochromism, mechanochromism and acidochromism. Furthermore, lipid droplets imaging investigation proved the compound 1 b‐3 was capable of achieving specific lipid droplets bioimaging. This work not only presents a better understanding of the structure‐fluorescent property relationship based on the scaffold of rofecoxib, but also provides a new avenue for spectral modulation and the development of new MSR materials.

Publisher

Wiley

Subject

General Chemistry

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