Chinese Journal of Organic Chemistry >
Cyanostilbene Bridged Triphenylene Dyad Stimuli-Responsive Discotic Liquid Crystal: Synthesis, Properties and Applications
Received date: 2023-02-23
Revised date: 2023-04-10
Online published: 2023-05-06
Supported by
National Natural Science Foundation of China(51773140); National Natural Science Foundation of China(51973143)
A dibranched cyanostilbene triphenylene dimer liquid crystal compound PBTPA with D-A structure was synthesized by the classical Knoevenagel and Suzuki coupling reaction, and characterized by nuclear magnetic resonance hydrogen spectrum (1H NMR) and carbon spectrum (13C NMR), and high resolution mass spectrometry (HRMS). PBTPA has excellent fluorescence emission in both solution and film states, showing obvious aggregation-induced emission enhancement effect, and the maximum fluorescence intensity is 4.2 times higher than the initial value. This effectively overcomes the drawbacks of aggregation-induced quenching of discotic molecules. PBTPA exhibits noticeable solvatochromic behavior from blue to orange in solvents with different polarities. The fluorescence emission wavelength is red-shifted by 110 nm, and the maximum absolute fluorescence quantum yield is as high as 74%. Density functional theory calculations show that there is outstanding charge transfer in PBTPA molecules. PBTPA has an obvious reversible grinding stimulation response. The fluorescence changes from yellow to orange before and after grinding. X-ray diffraction (XRD) and scanning electron microscope (SEM) prove that the process is accompanied by a crystal transformation. Based on this property, data rewriting paper can be designed easily with grinding and dichloromethane fuming, which can be used repeatedly by grinding and dichloromethane vapor fumigation. Additionally, PBTPA also has great liquid crystal properties, and polarizing optical microscopy (POM) texture appears apparently fan-shaped focal cone texture. With the change of temperature, it shows rectangular columnar phase to crystal phase, accompanied by fluorescence conversion, which is attributed to the change of viscosity and aggregation form. In addition, PBTPA is also a good electroluminescent material, and the color purity of yellow organic light-emitting diode prepared by PBTPA is as high as 99% at the turn-on voltage of 3.2 V. The highest luminous efficiency can reach 16 lm/W, so it has preeminent application potential in liquid crystal semiconductor, data processing, organic light emitting diode and other fields.
Chongyang Zeng , Ping Hu , Biqin Wang , Wenyan Fang , Keqing Zhao . Cyanostilbene Bridged Triphenylene Dyad Stimuli-Responsive Discotic Liquid Crystal: Synthesis, Properties and Applications[J]. Chinese Journal of Organic Chemistry, 2023 , 43(9) : 3287 -3296 . DOI: 10.6023/cjoc202302025
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