蒽取代氰基芪的合成表征及同质多晶的光学性质研究
Synthesis and Characterization of Cyano Substituted Anthracene Based Stilbene Derivatives and Optical Properties of Polymorphism
DOI: 10.12677/MS.2019.99110, PDF,  被引量    科研立项经费支持
作者: 谈惟烈, 陈 鹏, 蒋炳丽*:桂林医学院药学院,广西 桂林
关键词: 聚集诱导发光氰基芪同质多晶荧光Aggregation-Induced Emission Canyo-Stilbene Polymorphism Fluorescence
摘要: 有机发光材料在光电器件、生物化学检测、传感器等领域有着巨大的应用优势。本文设计合成一种新型蒽取代氰基芪(ASC)的有机发光化合物,通过溶剂交换法培养得到该化合物的两种不同单晶。采用高分辨核磁共振波谱仪和质谱仪对化合物进行化学结构表征,利用单晶分析仪对化合物的空间排列方式进行表征确定;此外还采用紫外光谱仪、荧光分光光度计对其光学性质进行了详细研究。研究结果表明,ASC在溶液状态下基本不发光(<1%),但是在结晶状态时光致发光强度显著增强,表现出结晶诱导发光特性;ASC的晶体具有同质多晶现象,两种不同晶体的群空间分别是P2(1)/C的单斜晶系和群空间为P-1的三斜晶系;ASC单斜晶系和三斜晶系的晶体在365 nm的紫外光激发下分别发射绿色和黄色荧光,荧光光谱发射峰值分别为505 nm和530 nm,绝对量子效率分别为18.83%和1.38%,表现出凝聚态结构依赖性的独特光学现象;ASC的同质多晶光学现象对新型有机光电材料、生物医学荧光探针材料的分子设计具有参考意义。
Abstract: Organic luminescent materials have great applications advantages in optoelectronic devices, bio-chemical detections, and sensors. In this paper, a novel anthracene-substituted cyanostilbene (ASC) organic luminescent compound was obtained, and its two different crystals were obtained by sol-vent exchange method. The chemical structures of ASC were characterized by high-resolution NMR spectrometers and mass spectrometers, the crystal structures were characterized using a single crystal analyzer. The optical properties were studied in detail by UV and fluorescence spectrometer. The results showed that ASC does not emit light (<1%) in solution state, but the photoluminescence intensity is significantly enhanced in the crystalline state, showing crystallization-induced lumines-cence properties; ASC crystals have polymorphism, and the monoclinic system with space P2(1)/C and the triclinic system with group space P-1; the crystals of ASC monoclinic and triclinic crystals emit yellow and yellow under 365 nm UV light, respectively. The green and yellow fluorescence emission peaks were 505 nm and 530 nm, respectively, and the absolute quantum efficiencies were 18.83% and 1.38%, respectively, showing a unique optical phenomenon of condensed structure dependence. Polymorphism of ASC provided a rational molecular design strategy for novel organic luminogens.
文章引用:谈惟烈, 陈鹏, 蒋炳丽. 蒽取代氰基芪的合成表征及同质多晶的光学性质研究[J]. 材料科学, 2019, 9(9): 890-897. https://doi.org/10.12677/MS.2019.99110

参考文献

[1] Hong, Y., Lam, J.W. and Tang, B.Z. (2011) Aggregation-Induced Emission. Chemical Society Reviews, 40, 5361-5388. [Google Scholar] [CrossRef] [PubMed]
[2] Thomas, S.W., Joly, G.D. and Swager, T.M. (2007) Chemical Sensors Based on Am-plifying Fluorescent Conjugated Polymers. Chemical Reviews, 107, 1339-1386. [Google Scholar] [CrossRef] [PubMed]
[3] Qin, W., Lam, J.W., Yang, Z., Chen, S., Liang, G., Zhao, W., Kwok, H.S. and Tang, B.Z. (2015) Red Emissive AIE Luminogens with High Hole-Transporting Properties for Efficient Non-Doped OLEDs. Chemical Communications, 51, 7321-7324. [Google Scholar] [CrossRef
[4] Liu, Y. and Bonizzoni, M. (2014) A Supramolecular Sensing Array for Qualitative and Quantitative Analysis of Organophosphates in Water. Journal of the American Chemical Society, 136, 14223-14229. [Google Scholar] [CrossRef] [PubMed]
[5] Lakowicz, J.R. (2007) Principles of Fluorescence Spectroscopy. Springer, Ber-lin.
[6] Gong, Y., Zhang, Y., Yuan, W.Z., Sun, J.Z. and Zhang, Y. (2014) D-A Solid Emitter with Crowded and Remarkably Twisted Conformations Exhibiting Multifunctionality and Multicolor Mechanochromism. The Journal of Physical Chemistry C, 118, 10998-11005. [Google Scholar] [CrossRef
[7] Yu, T., Ou, D., Wang, L., Zheng, S., Yang, Z., Zhang, Y., Chi, Z., Liu, S., Xu, J. and Aldred, M.P. (2017) A New Approach to Switchable Photochromic Materials by Combining Photochromism and Pie-zochromism Together in an AIE-Active Molecule. Materials Chemistry Frontiers, 1, 1900-1904. [Google Scholar] [CrossRef
[8] Gong, Y., Chen, G., Peng, Q., Yuan, W.Z., Xie, Y., Li, S., Zhang, Y. and Tang, B.Z. (2015) Achieving Persistent Room Temperature Phosphorescence and Remarkable Mechanochromism from Pure Organic Luminogens. Advanced Materials, 27, 6195-6201. [Google Scholar] [CrossRef] [PubMed]
[9] McCrone, W.C. (1965) Polymorphism. In: Fox, D., Labes, M.M. and Weissberger, A., Eds., Physics and Chemistry of the Organic Solid State, Vol. 2, Wiley-Interscience, New York, 725-767.
[10] Li, R., Xiao, S., Li, Y., Lin, Q., Zhang, R., Zhao, J., Yang, C., Zou, K., Li, D. and Yi, T. (2014) Polymorphism-Dependent and Piezochromic Luminescence Based on Molecular Packing of a Conjugated Molecule. Chemical Science, 5, 3922-3928. [Google Scholar] [CrossRef
[11] Kervyn, S., Fenwick, O., Di Stasio, F., Shin, Y.S., Wouters, J., Accorsi, G., Osella, S., Beljonne, D., Cacialli, F. and Bonifazi, D. (2013) Polymorphism, Fluorescence, and Optoelectronic Properties of a Borazine Derivative. Chemistry—A European Journal, 19, 7771-7779. [Google Scholar] [CrossRef] [PubMed]
[12] Huang, B., Chen, W.C., Li, Z., Zhang, J., Zhao, W., Feng, Y., Tang, B.Z. and Lee, C.S. (2018) Manipulation of Molecular Aggregation States to Realize Polymorphism, AIE, MCL, and TADF in a Single Molecule. Angewandte Chemie International Edition, 57, 12473-12477. [Google Scholar] [CrossRef] [PubMed]
[13] Qi, Q., Zhang, J., Xu, B., Li, B., Zhang, S.X.-A. and Tian, W. (2013) Mechanochromism and Polymorphism-Depen- dent Emission of Tetrakis (4-(dimethylamino) phenyl) Ethylene. The Journal of Physical Chemistry C, 117, 24997-25003. [Google Scholar] [CrossRef
[14] Yang, W., Liu, C., Lu, S., Du, J., Gao, Q., Zhang, R., Liu, Y. and Yang, C. (2018) AIE-Active Smart Cyanostyrene Luminogens: Polymorphism-Dependent Multicolor Mechanochromism. Journal of Materials Chemistry C, 6, 290-298. [Google Scholar] [CrossRef
[15] Morris, J.V., Mahaney, M.A. and Huber, J.R. (1976) Fluorescence Quantum Yield Determinations. 9,10-Diphenylan- thracene as a Reference Standard in Different Solvents. The Journal of Physical Chemistry, 80, 969-974. [Google Scholar] [CrossRef
[16] Luo, J., Xie, Z., Lam, J.W., Cheng, L., Chen, H., Qiu, C., Kwok, H.S., Zhan, X., Liu, Y. and Zhu, D. (2001) Aggregation-Induced Emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chemical Communications, 18, 1740-1741. [Google Scholar] [CrossRef] [PubMed]
[17] Gong, Y., Zhao, L., Peng, Q., Fan, D., Yuan, W.Z., Zhang, Y. and Tang, B.Z. (2015) Crystallization-Induced dual Emission from Metal- and Heavy Atom-Free Aromatic Acids and Esters. Chemical Science, 6, 4438-4444. [Google Scholar] [CrossRef
[18] Yoshii, R., Hirose, A., Tanaka, K. amd Chujo, Y. (2014) Functionalization of Boron Diiminates with Unique Optical Properties: Multicolor Tuning of Crystallization-Induced Emission and Introduction into the Main Chain of Conjugated Polymers. Journal of the American Chemical Society, 136, 18131-18139. [Google Scholar] [CrossRef] [PubMed]