Dual-state emissive imidazo[1,2-α]pyridines with full color emission, acidochromism, viscosity-dependent fluorescence, and bioimaging applications

被引:15
作者
Zhu, Yujie [1 ]
Liao, Kaihao [1 ]
Li, Yigao [1 ]
Zhang, Wenjing [1 ]
Song, Bing [1 ]
Hao, Xin-Qi [1 ]
Zhu, Xinju [1 ]
机构
[1] Zhengzhou Univ, Coll Chem, 100 Sci Rd, Zhengzhou 450001, Henan, Peoples R China
基金
中国国家自然科学基金;
关键词
Imidazo[1,2-alpha]pyridine; Dual-state emission; Full color emission; Acidochromism; Viscosity sensitivity; Cell imaging; AGGREGATION-INDUCED EMISSION; LIGHT-EMITTING-DIODES; SOLID-STATE; DESIGN; SUBSTITUENTS; LUMINESCENCE; SUPPRESSION; DERIVATIVES; MODULATION; BEHAVIORS;
D O I
10.1016/j.dyepig.2024.112004
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Five novel dual -state emissive imidazo[1,2-alpha]pyridine-based luminogens IP1-5 were rationally designed and prepared by varying the conjugation length and the nature of donor -acceptor (D -A) units. These D -A chromophores displayed cyan, green, yellow, and red fluorescence in the solid state, with full -color emission achieved for the first time through modification of imidazo[1,2-alpha]pyridine core. Interestingly, IP1 and IP5 in the solid state exhibited an abnormal remarkable blue -shift emission compared with those in THF, probably due to the highly twisted molecular conformations and solvent effect by theoretical calculations as well as crystal structure analyses. Importantly, IP1-5 revealed remarkable reversible acid -induced acidichromism, accompanied with dual change of colorimetric and fluorometric determination. Viscosity -dependent fluorescence was next conducted, indicting IP1-3 can be utilized for local viscosity detection. Moreover, IP1-5 served as promising candidates for multicolor bioimaging with low cell toxicity and good biocompatibility.
引用
收藏
页数:11
相关论文
共 103 条
[1]  
Auweter H, 1999, ANGEW CHEM INT EDIT, V38, P2188, DOI 10.1002/(SICI)1521-3773(19990802)38:15<2188::AID-ANIE2188>3.0.CO
[2]  
2-#
[3]   Arylstyrylimidazo[1,2-a]pyridine-based donor-acceptor acidochromic fluorophores: Synthesis, photophysical, thermal and biological properties [J].
Aydiner, Burcu ;
Yalcin, Ergin ;
Ihmels, Heiko ;
Arslan, Leyla ;
Acik, Leyla ;
Seferoglu, Zeynel .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2015, 310 :113-121
[4]   Dual-State Emission (DSE) in Organic Fluorophores: Design and Applications [J].
Belmonte-Vazquez, Jose L. ;
Amador-Sanchez, Yoarhy A. ;
Rodriguez-Cortes, Lizbeth A. ;
Rodriguez-Molina, Braulio .
CHEMISTRY OF MATERIALS, 2021, 33 (18) :7160-7184
[5]   Solid-state emitting twisted π-conjugate as AIE-active DSE-gen: in vitro anticancer properties against FaDu and 4T1 with biocompatibility and bioimaging [J].
Bhuin, Shouvik ;
Sharma, Pravesh ;
Chakraborty, Purbali ;
Kulkarni, Onkar Prakash ;
Chakravarty, Manab .
JOURNAL OF MATERIALS CHEMISTRY B, 2022, 11 (01) :188-203
[6]   NNN Pincer Ru(II)-Complex-Catalyzed α-Alkylation of Ketones with Alcohols [J].
Cao, Xiao-Niu ;
Wan, Xiao-Min ;
Yang, Fa-Liu ;
Li, Ke ;
Hao, Xin-Qi ;
Shao, Tian ;
Zhu, Xinju ;
Song, Mao-Ping .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (07) :3657-3668
[7]   Progress in the Development of Imidazopyridine-Based Fluorescent Probes for Diverse Applications [J].
Chaudhran, Preeti AshokKumar ;
Sharma, Abha .
CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY, 2024, 54 (07) :2148-2165
[8]   Conjugation-Induced Rigidity in Twisting Molecules: Filling the Gap Between Aggregation-Caused Quenching and Aggregation-Induced Emission [J].
Chen, Gan ;
Li, Wenbo ;
Zhou, Tianru ;
Peng, Qian ;
Zhai, Di ;
Li, Hongxiang ;
Yuan, Wang Zhang ;
Zhang, Yongming ;
Tang, Ben Zhong .
ADVANCED MATERIALS, 2015, 27 (30) :4496-4501
[9]   Molecular Cursor Caliper: A Fluorescent Sensor for Dicarboxylate Dianions [J].
Chen, Wei ;
Guo, Chenxing ;
He, Qing ;
Chi, Xiaodong ;
Lynch, Vincent M. ;
Zhang, Zhiyun ;
Su, Jianhua ;
Tian, He ;
Sessler, Jonathan L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (37) :14798-14806
[10]   Full-Color Emissive D-D-A Carbazole Luminophores: Red-to-NIR Mechano-fluorochromism, Aggregation-Induced Near-Infrared Emission, and Application in Photodynamic Therapy [J].
Chen, Zhao ;
Qin, Huan ;
Yin, Ya ;
Deng, Dian-dian ;
Qin, Si-Yong ;
Li, Nan ;
Wang, Kai ;
Sun, Yue .
CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (11)