Malonitrile‐Functionalized Tetraphenylpyrazine: Aggregation‐Induced Emission, Ratiometric Detection of Hydrogen Sulfide, and Mechanochromism

• Published in: Advanced functional materials 2018-02, Vol.28 (6), p.n/a
• Main Authors: Chen, Ming, Chen, Rui, Shi, Yang, Wang, Jianguo, Cheng, Yanhua, Li, Ying, Gao, Xuedong, Yan, Yun, Sun, Jing Zhi, Qin, Anjun, Kwok, Ryan T. K., Lam, Jacky W. Y., Tang, Ben Zhong
• Format: Article
• Language: English
• Subjects: Agglomeration; aggregation‐induced emission; Biosensors; Diodes; Emission; Fluorescence; Hydrogen sulfide; Light emitting diodes; Materials science; mechanochromism; Mechanoluminescence; Medical imaging; Organic light emitting diodes; sensors; tetraphenylpyrazine
• ISSN: 1616-301X; 1616-3028
• DOI: 10.1002/adfm.201704689

Development of new aggregation‐induced emission (AIE) luminogens has been a hot research topic because they thoroughly solve the notorious aggregation‐caused quenching effect confronted in conventional fluorogens and their promising applications in, for example, organic light‐emitting diodes, chemo‐ and biosensors and bioimaging. Many AIE luminogens (AIEgens) have been prepared but most of them are silole, tetraphenylethene, distyrylanthracene, and their derivatives. In this work, based on the skeleton of tetraphenylpyrazine (TPP), a new AIEgen, named TPP‐PDCV, is generated by functionalizing TPP with malonitrile group. TPP‐PDCV can serve as a sensitive ratiometric fluorescent probe for detecting hydrogen sulfide with high speciality and low detection limit of down to 0.5 × 10−6m. The mechanism for such detection is fully investigated and deciphered. Unlike most reported mechanochromic AIEgens, which undergo turn‐off or ‐on emission or emission bathochromic shift in the presence of external stimuli, TPP‐PDCV exhibits an abnormal and reversible mechanochromism with hypsochromic effect. These indicate that TPP‐PDCV possesses a huge potential for high‐tech applications through rational modification of TPP core. A tetraphenylpyrazine‐based aggregation‐induced emission luminogen (AIEgen) with malonitrile functionality can function as a ratiometric fluorescent probe to detect hydrogen sulfide with fast response, high sensitivity, and good selectivity. It also displays a reversible mechanochromism with a hypsochromic effect in the presence of external stimuli, which is rarely observed in previously reported AIEgens.