Near-Infrared Thienoisoindigos with Aggregation-Induced Emission: Molecular Design, Optical Performance, and Bioimaging Application

被引:33
作者
Chen, Weijie [1 ,2 ,3 ,4 ]
Zhang, Chen [5 ]
Chen, Huijuan [1 ,2 ,3 ,4 ]
Zang, Kun [5 ]
Liu, Sheng Hua [1 ,2 ,3 ,4 ]
Xie, Yuan [6 ]
Tan, Ying [5 ]
Yin, Jun [1 ,2 ,3 ,4 ,6 ,7 ]
机构
[1] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China
[2] Cent China Normal Univ, Hubei Int Sci & Technol Cooperat Base Pesticide &, Wuhan, Peoples R China
[3] Cent China Normal Univ, Int Joint Res Ctr Intelligent Biosensing Technol, Wuhan 430079, Peoples R China
[4] Cent China Normal Univ, Coll Chem, Wuhan 430079, Peoples R China
[5] Tsinghua Univ, Grad Sch Shenzhen, State Key Lab Chem Oncogen, Key Lab Chem Biol, Shenzhen 518055, Guangdong, Peoples R China
[6] Guangdong Prov Key Lab Radioact & Rare Resource U, Shaoguan 512026, Peoples R China
[7] Hubei Univ, Minist Educ Key Lab Synth & Applicat Organ Funct, Wuhan 430062, Peoples R China
基金
中国国家自然科学基金;
关键词
FLUORESCENT-PROBES; AIE LUMINOGENS; DYE; BEHAVIOR; MECHANOCHROMISM; CONSTRUCTION; ENHANCEMENT; PROGRESS;
D O I
10.1021/acs.analchem.0c04260
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Thienoisoindigo as a popular conjugated skeleton has been constantly applied in the construction of organic optoelectronic materials. Exploring its new applications in fluorescent sensors and bioimaging is helpful to extend its potential. In this work, a thienoisoindigo fluorophore was first selected as a building block to be applied in the construction of the near-infrared fluorescent materials with an aggregation-induced emission manner through introducing triarylamine, thiophene-bridged triarylamine, and N,N-dimethyl styrene, respectively. These fluorescent agents showed the near-infrared emission and possessed typical aggregation-induced emission behavior. Although they had low band gaps and near-infrared emission, they presented remarkable photostability. Especially, thiophene-bridged triarylamine and N,N-dimethyl styrene-coated thienoisoindigos exhibited strong lysosomal targeting capability, and they could also serve for fluorescence imaging in vivo.
引用
收藏
页码:3378 / 3385
页数:8
相关论文
共 67 条
[1]   Ionic Aggregation-Induced Emission: Bulky Hydrophobic Counterions Light Up Dyes in Polymeric Nanoparticles [J].
Aparin, Ilya O. ;
Melnychuk, Nina ;
Klymchenko, Andrey S. .
ADVANCED OPTICAL MATERIALS, 2020, 8 (14)
[2]   A new thiophene substituted isoindigo based copolymer for high performance ambipolar transistors [J].
Ashraf, Raja Shahid ;
Kronemeijer, Auke Jisk ;
James, David Ian ;
Sirringhaus, Henning ;
McCulloch, Iain .
CHEMICAL COMMUNICATIONS, 2012, 48 (33) :3939-3941
[3]   Detection of Lysosome by a Fluorescent Heterocycle: Development of Fused Pyrido-Imidazo-Indole Framework via Cu-Catalyzed Tandem N-Arylation [J].
Banerji, Biswadip ;
Chatterjee, Satadru ;
Chandrasekhar, Kadaiahgari ;
Ghosh, Saswati ;
Mukherjee, Kaustuv ;
Mandal, Chitra .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (21) :13011-13018
[4]   Aggregation-Induced Emission: Recent Advances in Materials and Biomedical Applications [J].
Cai, Xiaolei ;
Liu, Bin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (25) :9868-9886
[5]   Optical nano-agents in the second near-infrared window for biomedical applications [J].
Cai, Yu ;
Wei, Zheng ;
Song, Chuanhui ;
Tang, Chuanchao ;
Han, Wei ;
Dong, Xiaochen .
CHEMICAL SOCIETY REVIEWS, 2019, 48 (01) :22-37
[6]   Ultrafast and Noninvasive Long-Term Bioimaging with Highly Stable Red Aggregation-Induced Emission Nanoparticles [J].
Che, Weilong ;
Zhang, Liping ;
Li, Yuanyuan ;
Zhu, Dongxia ;
Xie, Zhigang ;
Li, Guangfu ;
Zhang, Pengfei ;
Su, Zhongmin ;
Dou, Chuandong ;
Tang, Ben Zhong .
ANALYTICAL CHEMISTRY, 2019, 91 (05) :3467-3474
[7]   Thienoisoindigo-Based Dopant-Free Hole Transporting Material for Efficient p-i-n Perovskite Solar Cells with the Grain Size in Micrometer Scale [J].
Chen, Chih-Hsin ;
Hsu, Yu-Ting ;
Wang, Bo-Cheng ;
Chung, Chung-Lin ;
Chen, Chih-Ping .
JOURNAL OF PHYSICAL CHEMISTRY C, 2019, 123 (03) :1602-1609
[8]   Vinyl-functionalized multicolor benzothiadiazoles: design, synthesis, crystal structures and mechanically-responsive performance [J].
Chen, Jianhua ;
Ye, Fengying ;
Lin, Yan ;
Chen, Zhao ;
Liu, Shenghua ;
Yin, Jun .
SCIENCE CHINA-CHEMISTRY, 2019, 62 (04) :440-450
[9]   A Highly Reversible Mechanochromic Difluorobenzothiadiazole Dye with Near-Infrared Emission [J].
Chen, Jianhua ;
Li, Dongyang ;
Chi, Weijie ;
Liu, Guotao ;
Liu, Sheng Hua ;
Liu, Xiaogang ;
Zhang, Chun ;
Yin, Jun .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (15) :3671-3676
[10]   Fluorescent probes for pH and alkali metal ions [J].
Chen, Weijie ;
Ma, Xiaoxie ;
Chen, Huijuan ;
Liu, Sheng Hua ;
Yin, Jun .
COORDINATION CHEMISTRY REVIEWS, 2021, 427