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

被引：161

作者：

Chen, Ming ^{[1
,2
,3
]}

Chen, Rui ^{[4
]}

Shi, Yang ^{[4
]}

Wang, Jianguo ^{[1
,2
,3
]}

Cheng, Yanhua ^{[1
,2
,3
]}

Li, Ying ^{[1
,2
,3
]}

Gao, Xuedong ^{[5
]}

Yan, Yun ^{[5
]}

Sun, Jing Zhi ^{[4
]}

Qin, Anjun ^{[6
]}

Kwok, Ryan T. K. ^{[1
,2
,3
]}

Lam, Jacky W. Y. ^{[1
,2
,3
]}

Tang, Ben Zhong ^{[1
,2
,3
,6
]}

机构：

[1] Hong Kong Univ Sci & Technol, Hong Kong Branch,State Key Lab Mol Neurosci, Chinese Natl Engn Res Ctr Tissue Restorat & Recon, Inst Adv Study,Div Biomed Engn,Div Life Sci, Kowloon, Hong Kong, Peoples R China

[2] Hong Kong Univ Sci & Technol, Inst Mol Funct Mat, Kowloon, Hong Kong, Peoples R China

[3] HKUST Shenzhen Res Inst, Guangdong Prov Key Lab Brain Sci Dis & Drug Dev, Shenzhen 518057, Peoples R China

[4] Zhejiang Univ, Dept Polymer Sci & Engn, MOE Key Lab Macromol Synth & Functionalizat, Hangzhou 310027, Zhejiang, Peoples R China

[5] Peking Univ, Beijing Natl Lab Mol Sci, State Key Lab Struct Chem Unstable & Stable Speci, Coll Chem & Mol Engn, Beijing 100871, Peoples R China

[6] South China Univ Technol, State Key Lab Luminescent Mat & Devices, Guangdong Innovat Res Team, Guangzhou 510640, Guangdong, Peoples R China

来源：

ADVANCED FUNCTIONAL MATERIALS | 2018年 / 28卷 / 06期

基金：

中国国家自然科学基金;

关键词：

aggregation-induced emission; hydrogen sulfide; mechanochromism; sensors; tetraphenylpyrazine; FLUORESCENT-PROBE; FACILE PREPARATION; THIOL OXIDATION; RAPID DETECTION; LIVING CELLS; LUMINESCENCE; LUMINOGENS; SOLVATOCHROMISM; NEUROMODULATOR; NANOPARTICLES;

D O I：

10.1002/adfm.201704689

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 x 10(-6) m. 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.

引用

页数：10

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