Chinese Journal of Organic Chemistry >
Near-Infrared Aggregation-Induced Emission (AIE) Molecules Based on Coupling of Triarylamine-Modified Benzothiadiazole Units
Received date: 2024-07-05
Revised date: 2024-08-14
Online published: 2024-09-27
Supported by
National Natural Science Foundation of China(92056115)
Three new near-infrared (NIR) aggregation-induced emission (AIE) molecules were constructed by palladium- catalyzed coupling reaction with triarylamine modified benzothiadiazole as a donnor-acceptor (D-A) unit. Their structures were charaterized by 1H NMR, 13C NMR and HRMS. The results of absorption spectroscopic and fluorescence spectroscopic measurements indicated that the absorption maxima of these three compounds in dichloromethean solution were at 525, 521 and 495 nm, respectively, while their emission bands were located at 600~1050 nm. Solvent-dependent spectrosopic studies and theorectical calculations revealed intramolecular charge transfer (ICT) charateristics of these compounds. These compounds exhibited NIR AIE in tetrahydrofuran (THF)/H2O with emission wavelengths 600~1000 nm and fluorescence quantum yields up to 13%, 10% and 4%, respectively. The results of dynamic light scattering (DLS) and atomic force microscope (AFM) showed that compounds 1~3 formed spherical aggregates of about 80 nm in THF/H2O (V∶V=8∶2).
Zixuan Dong , Junjun Su , Hongfei Pan , Xiangkui Ren , Zhijian Chen . Near-Infrared Aggregation-Induced Emission (AIE) Molecules Based on Coupling of Triarylamine-Modified Benzothiadiazole Units[J]. Chinese Journal of Organic Chemistry, 2025 , 45(1) : 205 -211 . DOI: 10.6023/cjoc202407014
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