有机共晶非线性光学材料及应用研究进展

doi:10.6023/A22100411

化学学报 ›› 2023, Vol. 81 ›› Issue (2): 191-206.DOI: 10.6023/A22100411 上一篇下一篇

综述

有机共晶非线性光学材料及应用研究进展

郝良朦^a, 朱伟钢^a^,^b^,^*()

a 天津市分子光电科学重点实验室天津大学理学院化学系天津 300072
b 电子科技大学电子薄膜与集成器件国家重点实验室成都 610054

投稿日期:2022-10-01 发布日期:2022-11-08
通讯作者: 朱伟钢

作者简介:

郝良朦, 1999年出生于山东菏泽, 2021年获山东师范大学化学化工与材料科学学院学士学位后, 考研至天津大学理学院化学系, 目前主要研究方向为制备有机共晶材料, 重点在非线性光学领域的应用研究.

朱伟钢, 天津大学英才副教授、特聘研究员、博士生导师, 2011年本科毕业于电子科技大学, 2016年博士毕业于中国科学院化学研究所, 2016~2019年在美国西北大学化学系开展博士后研究, 师从Tobin J. Marks教授, 2020年起在天津大学理学院化学系开展教学科研工作. 研究方向包括超快时间分辨光谱、电子顺磁共振、有机电子学器件、非线性光学和金属氧化物.

基金资助:
电子薄膜与集成器件国家重点实验室开放课题(KFJJ202001)

Research Progress on Organic Cocrystals Nonlinear Optics Materials and Applications

Liangmeng Hao^a, Weigang Zhu^a^,^b()

a Department of Chemistry, School of Science, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Tianjin University, Tianjin 300072
b State Key Laboratory of Electronic Thin Films and Integrated Devices, University of Electronic Science and Technology of China, Chengdu 610054

Received:2022-10-01 Published:2022-11-08
Contact: Weigang Zhu
Supported by:
Open Foundation of State Key Laboratory of Electronic Thin Films and Integrated Devices(KFJJ202001)

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摘要/Abstract

随着二次谐波(SHG)和双光子吸收(TPA)的产生, 有机非线性光学(NLO)材料近十年来在激光频率转换、生物成像、微纳加工、光限幅以及太赫兹波(THz)等领域发挥越来越重要的应用, 引起了广泛兴趣. 迄今为止, 报道的绝大多数有机非线性光学活性材料为单一组分, 它们化学合成繁琐、实验条件苛刻且难以打破单一组分固有属性的限制. 而复合材料可通过共混、掺杂、共结晶等简易形式迅速地拓宽新材料种类, 通过一种分子以上基于分子间非共价相互作用的有机共晶已在很大程度上朝着调节和修改分子固体的物理化学性质的方向发展. 然而, 目前国内外并没有关于有机共晶在非线性光学领域中的系统性总结与介绍. 本综述首先介绍二阶、三阶非线性光学性能参数及其测试方法; 接着, 介绍共晶材料在该领域的最新研究进展, 包括材料的种类、制备方法、产生光学非线性效应的机理等; 其次, 讨论共晶非线性光学材料潜在的应用; 最后, 对该领域的发展提供了一些展望, 希望能为有机共晶与非线性光学领域的同行研究者们提供一定的借鉴参考.

关键词: 有机分子共晶, 非线性光学, 二次谐波, 双光子吸收, 太赫兹波

With the appearance of second harmonic generation (SHG) and two-photon absorption (TPA), organic nonlinear optical (NLO) materials have played an increasingly important role in laser frequency conversion, biological imaging, micro- nano processing, optical limiting, terahertz wave (THz) and other fields in the past decades, arousing widespread interest. So far, most of the organic nonlinear optical active materials reported are single component which chemical synthesis is cumbersome, experimental conditions are rigorous and it is difficult to break the limit of the inherent properties of the single component. While organic composite material can rapidly broaden the variety of materials through simple forms such as blending, doping and cocrystallization, organic cocrystals based on intermolecular non-covalent interactions through more than one molecule have been developed to a large extent towards tuning and modifying the physicochemical properties of molecular solids. However, there is no systematic introduction of organic cocrystals in nonlinear optics at home and abroad. Firstly, the second-order and third-order nonlinear optical performance parameters and their testing methods are introduced; then, the latest research progress of molecular cocrystals materials in this field is introduced, including the types of materials, preparation methods, and the mechanism of optical nonlinearity effect; next, the possible applications of cocrystals nonlinear optical materials are discussed. Finally, some prospects for the development of this field are provided, and it is believed that this review can provide some reference for researchers in the field of organic cocrystals and nonlinear optics.

Key words: organic molecular cocrystals, nonlinear optics, second harmonic generation, two-photon absorption, terahertz waves

引用此文

郝良朦, 朱伟钢. 有机共晶非线性光学材料及应用研究进展[J]. 化学学报, 2023, 81(2): 191-206.

Liangmeng Hao, Weigang Zhu. Research Progress on Organic Cocrystals Nonlinear Optics Materials and Applications[J]. Acta Chimica Sinica, 2023, 81(2): 191-206.

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图/表 13

图1. 非线性光学材料的发展趋势

Figure 1. Development trend of nonlinear optics materials. Reproduced with the permission from ref.[76]. Copyright 2011 Wiley-VCH. Reproduced with the permission from ref.[35]. Copyright 2017 Wiley-VCH. Reproduced with the permission from ref.[94]. Copyright 2020 Nature Publishing Group

图2. (a) 异构循环, (b) 全光极化和(c) 电晕极化示意图

Figure 2. Schematic diagram of (a) heterogeneous cycle, (b) all-optical polarization and (c) corona polarization

图3. (a) 上转换荧光法, (b) 非线性透过率法和(c) Z-扫描法测试示意图

Figure 3. Schematic diagram of (a) up-conversion fluorescence test, (b) nonlinear transmittance method test and (c) Z-scan method test

方法	晶系	点群	非线性光学性质	参考文献
溶剂缓慢挥发	单斜	P2₁/c	TPA	[34]
溶液法	—	—	TPA+AIE	[78]
固体研磨	六方	P6₅	TPA	[86]
滴铸法	三斜	P-1	TPA	[35]
溶剂缓慢冷却	单斜	Cc	SHG+THz	[98]
溶剂缓慢冷却	单斜	Cc	SHG+THz	[98]
液体辅助研磨	单斜	P2₁/c	TPA+AIE	[79]
溶剂缓慢挥发	单斜	P2₁/c	SHG	[30]
溶剂缓慢挥发	正交	Pca2₁	SHG	[75]
液体辅助研磨	单斜	P2₁/n	TPA	[76]

表1. 有机非线性光学共晶材料的代表性例子

Table 1. Representative examples of organic nonlinear optics cocrystal material

图4. (a) IFB, Bpe和F4DIB的分子结构. (b) Bpe-IFB和(c) Bpe-F4DIB的分子堆叠结构. (d) Bpe-IFB和(e) Bpe-F4DIB的共聚焦激光扫描显微镜(CLSM)图像

Figure 4. (a) Chemical structures of IFB, Bpe and F4DIB. Molecular packing structures of (b) Bpe-IFB and (c) Bpe-F4DIB. Confocal laser scanning microscopy (CLSM) images of (d) Bpe-IFB and (e) Bpe-F4DIB. Reproduced with permission from ref.[72]. Copyright 2015 American Chemical Society

图5. (a) Npe, F4DIB和Spe的分子结构. NFC的(b) 分子间相互作用和(c) 分子堆叠结构. (d) Npe和(e) NFC的上转换光致发光光谱

Figure 5. (a) Chemical structures of Npe, F4DIB and Spe. (b) Intermolecular interactions and (c) molecular packing structures of NFC. The up-conversion PL spectra of (d) Npe and (e) NFC. Reproduced with permission from ref.[34]. Copyright 2016 Wiley-VCH

图6. (a) A~E的分子结构. (b) 2A-E和(c) 2A-C的分子间相互作用. 上转换光致发光光谱(d) 2A-E, (e) 2A-C, (f) B-2D和(g) B-C

Figure 6. (a) Chemical structures of A~E. The intermolecular interactions of (b) 2A-E and (c) 2A-C. The up-conversion PL spectra of (d) 2A-E and (e) 2A-C. Reproduced with permission from ref.[75]. Copyright 2016 Royal Society of Chemistry. The up-conversion PL spectra of (f) B-2D and (g) B-C. Reproduced with permission from ref.[76]. Copyright 2011 Wiley-VCH

图7. (a) Npe, 4-溴代四氟苯甲酸, ACA和TCNB的分子结构. (b) Npe-C的双光子荧光光谱. (c) ACA-TCNB在不同泵浦强度下由800 nm激光器激发的双光子荧光光谱图, 插图显示了强度随泵强度的增加而变化. (d) Npe-C在不同含水量的荧光强度变化. (e) ACA-TCNB在丙酮-水溶液(φw=0~95%)中的荧光强度图, 插图代表在365 nm紫外线灯照射下拍摄的不同比例丙酮-水混合物的照片

Figure 7. (a) Chemical structures of Npe, 4-bromotetrafluorobenzoic acid, ACA and TCNB. (b) Two-photon fluorescence spectra of Npe-C. (c) Two-photon fluorescence spectra figure of ACA-TCNB excited by a 800 nm laser under different pump intensities. Insets show the changes in intensity with increasing pump intensity. (d) Fluorescence intensity changes of Npe-C at different water contents. Reproduced with permission from ref.[78]. Copyright 2018 Wiley-VCH. (e) Fluorescence intensity of ACA-TCNB in acetone-water mixtures (φw=0~95%), the insets represent photos of different ratios of acetone-water mixtures taken under 365 nm UV lamp. Reproduced with permission from ref.[79]. Copyright 2016 Royal Society of Chemistry

图8. (a) Acr和DNB的分子结构以及Acr-DNB的颜色. (b) Acr-DNB的分子间相互作用. (c) 在自然光下无机械作用下反应60 h后形成的共晶. (d) 共晶Acr-DNB的双光子激发范围. (f) YFP和Tyr203的分子间相互作用. (g) YFP和Try203在不同分子距离下的TPA截面

Figure 8. (a) Chemical structures of Spe and TCNB and the color of Acr-DNB. (b) The intermolecular interactions of Acr-DNB. (c) The cocrystal was obviously formed after reaction for 60 h under natural light and non-mechanical action. (d) The two-photon excitation window of Acr-DNB cocrystals. Reproduced with permission from ref.[86]. Copyright 2022 Royal Society of Chemistry. (f) The intermolecular interactions of YFP and Tyr203. (g) TPA cross sections of YFP and Try203 at different molecular distances. Reproduced with permission from ref.[87]. Copyright 2014 Royal Society of Chemistry

图9. (a) Spe和TCNB的分子结构和颜色. (b) STC的分子间相互作用. (c) 共晶STC的双光子激发范围. STC的(d) 吸收和发射光谱, (e) 拉曼光谱, (f) 基态和激发态的ESR光谱, (g) 基态和激发态的ESR光谱和(e)固态13C NMR谱

Figure 9. (a) Chemical structures and color of Spe and TCNB. (b) The intermolecular interactions of cocrystals STC. (c) The two-photon excitation window of STC cocrystals. (d) The absorption and PL spectra, (e) Raman spectra, (f) the ground and excited state ESR spectra, (g) solid- state 13C NMR spectra of STC cocrystal. Reproduced with permission from ref.[35]. Copyright 2017 Wiley-VCH

图10. (a) NDI-Δ和(c) COR的分子结构. (b) CNC-T和(d) CNC-Q的荧光光谱图. (e) NDI-Δ, (f) COR, (g) CNC-T和 (h) CNC-Q的双光子激发光谱

Figure 10. Chemical structures of (a) NDI-Δ and (c) COR. Fluorescence microscopy images of (b) CNC-T and (d) CNC-Q. Two-photon excited spectra of (e) NDI-Δ, (f) COR, (g) CNC-T and (h) CNC-Q. Reproduced with permission from ref[94]. Copyright 2020 Nature Publishing Group

图11. (a) OHQ-CBS和OHQ-T的分子结构. (b) OHQ-CBS:T(物质的量比1:6)的图片. (c) OHQ-CBS和(d) OHQ-T的空间点群. 粉末SHG测试(e) OHQ-CBS:T(物质的量比1:5), (f) OHQ-CBS:T(物质的量比1:6). 0.92 mm厚的OHQ-CBS:T(物质的量比1:6)共晶体中的THz产生(g)时间追踪, (h)傅里叶变换光谱

Figure 11. (a) Chemical structures of OHQ-CBS and OHQ-T. (b) The photograph of OHQ-CBS:T (molar ratio 1:6). The space group of (c) OHQ-CBS and (d) OHQ-T. Powder SHG of (e) OHQ-CBS:T (molar ratio 1:5), (f) OHQ-CBS: T (molar ratio 1:6). THz wave generation in 0.92 mm thick OHQ-CBS:T (molar ratio 1:6) cocrystal (g) time traces, (h) Fourier-transform spectra. Reproduced with permission from ref.[98]. Copyright 2018 Wiley-VCH

图12. (a) NP1和(b) 3a~3c的分子结构. (c) Iblue/Igreen与pH的拟合曲线. (d) 20 mmol/L NP1标记胃和食管炎组织的双光子荧光光谱图像. (e) 根据Iblue/Igreen比值和荧光滴定曲线估计的pH值. (f) Z-扫描透过率曲线

Figure 12. Chemical structures of (a) NP1 and (b) 3a~3c. (c) Fitted curve of Iblue/Igreen and pH. (d) TPM images of stomach and esophagitis tissues labeled with 20 mmol/L NP1. (e) The pH values that were estimated from the Iblue/Igreen ratios and fluorescence titration curve. Reproduced with permission from ref.[109]. Copyright 2012 Wiley-VCH. (f) Z-scan transmittance curve. Reproduced with permission from ref.[114]. Copyright 2013 Elsevier

参考文献 116

[1]	Franken, P. A.; Hill, A. E.; Peters, C. W.; Weinreich, G. Phys. Rev. Lett. 1961, 7, 118. doi: 10.1103/PhysRevLett.7.118
[2]	Ashkin, A.; Boyd, G. D.; Dziedzic, J. M.; Smith, R. G.; Ballman, A. A.; Levinstein, J. J.; Nassau, K. Appl. Phys. Lett. 1966, 9, 72. doi: 10.1063/1.1754607
[3]	Gong, Y.-P.; Hu, C.-L.; Ma, Y.-X.; Mao, J.-G.; Kong, F. Inorg. Chem. Front. 2019, 6, 3133. doi: 10.1039/C9QI00936A
[4]	Liu, T.; Zhang, D.; Huqe, M. R.; Wang, W.; Zapien, J. A.; Tsang, S.-W.; Luo, J. Sci. China. Chem. 2021, 65, 584. doi: 10.1007/s11426-021-1164-4
[5]	Bonaccorso, F.; Sun, Z.; Hasan, T.; Ferrari, A. C. Nat. Photonics. 2010, 4, 611. doi: 10.1038/nphoton.2010.186
[6]	Ganeev, R. A. Nonlinear Optical Properties of Materials, Springer, London, 2012, p. xiv.
[7]	Shi, R.; Han, X.; Xu, J.; Bu, X.-H. Small. 2021, 17, e2006416.
[8]	Risk, W. P.; Lau, S. D. Appl. Phys. Lett. 1996, 69, 3999. doi: 10.1063/1.117850
[9]	David, C. H. Opt. Lett. 1998, 23, 171. doi: 10.1364/OL.23.000171
[10]	Nash, F. R.; Bergman, J. G.; Boyd, G. D.; Turner, E. H. J. Appl. Phys. 1969, 40, 5201.
[11]	Chen, C. Sci. China Ser. B. 1984, 14, 598.
[12]	Wang, J.; Chen, C. J. Mater. Res. 2003, 18, 2479.
[13]	Tadashi, T.; Chen, C. Opt. Lett. 2003, 28, 254. pmid: 12653363
[14]	Lahav, M.; Kucharczyk, W. Cryst. Res. Technol. 1999, 34, 745. doi: 10.1002/(SICI)1521-4079(199906)34:5/6＜745::AID-CRAT745＞3.0.CO;2-X
[15]	Kenneth, H. IEEE J. Quantum Elect. 1968, 4, 243. doi: 10.1109/JQE.1968.1075307
[16]	Liu, H.; Cheng, L. Appl. Optics. 1988, 27, 1006. doi: 10.1364/AO.27.001006 pmid: 20531509
[17]	Hong, Y.; Zhang, H. Opt. Lett. 1993, 18, 772. pmid: 19802268
[18]	Shi, S.; Chen, G. Nonlinear Optics. Xidian University, Xi'an, 2012, p. 78.
[19]	Tang, R.-L.; Zhou, S.-M.; Cheng, Z.-Y.; Yu, G.; Peng, Q.; Zeng, H.- Y.; Li, Q.-Q.; Li, Z. Chem. Sci. 2017, 8, 340. doi: 10.1039/C6SC02956F
[20]	Li, Z.-A.; Chen, P.-Y.; Xie, Y.-J.; Li, Z.; Qin, J.- G. Adv. Electron. Mater. 2017, 3, 1700138. doi: 10.1002/aelm.201700138
[21]	Kong, L.; Zhong, M.; Shuang, W.; Xu, Y.; Bu, X.- H. Chem. Soc. Rev. 2020, 49, 2378. doi: 10.1039/C9CS00880B
[22]	Medishetty, R.; Zareba, J. K.; Mayer, D.; Samoc, M.; Fischer, R. A. Chem. Soc. Rev. 2017, 46, 4976. doi: 10.1039/C7CS00162B
[23]	Mingabudinova, L. R.; Vinogradov, V. V.; Milichko, V. A.; Hey-Hawkins, E.; Vinogradov, A. V. Chem. Soc. Rev. 2016, 45, 5408. pmid: 27711673
[24]	Xiong, J.; Qian, X.; Zhao, L.; Xu, J. Inorg. Chem. Commun. 2019, 105, 20. doi: 10.1016/j.inoche.2019.04.027
[25]	Hafez, H. A.; Chai, X.; Ibrahim, A.; Mondal, S.; Férachou, D.; Ropagnol, X.; Ozaki, T. J. Opt. 2016, 18, 4. doi: 10.1007/BF03549190
[26]	Sivakumar, T.; Anbarasan, R.; Kalyana Sundar, J.; Anna Lakshmi, M. J. Mater. Sci. Mater. Electron. 2020, 31, 12943. doi: 10.1007/s10854-020-03847-0
[27]	Sivakumar, T.; Eniya, P.; Sundar, J. K.; Thirunavukkarasu, A.; Lakshmi, M. A.; Kanthimathi, G. Cryst. Res. Technol. 2021, 56, 2100016. doi: 10.1002/crat.202100016
[28]	Xu, Y.; Wang, W.; Ge, Y.; Guo, H.; Zhang, X.; Chen, S.; Deng, Y.; Lu, Z.; Zhang, H. Adv. Funct. Mater. 2017, 27, 1702437. doi: 10.1002/adfm.201702437
[29]	Wang, S.; Shen, B.; Wei, H.-L.; Liu, Z.; Chen, Z.; Zhang, Y.; Su, Y.; Zhang, J.-Z.; Wang, H.; Su, Q. Nanoscale. 2019, 11, 10220. doi: 10.1039/C9NR02493J
[30]	Yan, D.; Yang, H.; Meng, Q.; Lin, H.; Wei, M. Adv. Funct. Mater. 2013, 24, 587. doi: 10.1002/adfm.201302072
[31]	Zhao, J.; Huang, W. Aerosp. Sci. Technol. 1998, 1, 16.
[32]	Jiang, M.; Zhen, C.; Li, S.; Zhang, X.; Hu, W. Front. Chem. 2021, 9, 764628. doi: 10.3389/fchem.2021.764628
[33]	Shi, S.; Chen, G. Nonlinear Optics. Xidian University, Xi'an, 2012, p. 3.
[34]	Zhu, W.-G.; Zhu, L.-Y.; Sun, L.-J.; Zhen, Y.-G.; Dong, H.-L.; Wei, Z.-X.; Hu, W.-P. Angew. Chem., Int. Ed. 2016, 55, 14023. doi: 10.1002/anie.201607712
[35]	Sun, L.-J.; Zhu, W.-G.; Wang, W.; Yang, F.-X.; Zhang, C.-C.; Wang, S.-F.; Zhang, X.-T.; Li, R.-J.; Dong, H.-L.; Hu, W.-P. Angew. Chem., Int. Ed. 2017, 56, 7831. doi: 10.1002/anie.201703439
[36]	Aitipamula, S.; Banerjee, R.; Bansal, A. K.; Biradha, K.; Cheney, M. L.; Choudhury, A. R.; Desiraju, G. R.; Dikundwar, A. G.; Dubey, R.; Duggirala, N.; Ghogale, P. P.; Ghosh, S.; Goswami, P. K.; Goud, N. R.; Jetti, R. R. K. R.; Karpinski, P.; Kaushik, P.; Kumar, D.; Kumar, V.; Moulton, B.; Mukherjee, A.; Mukherjee, G.; Myerson, A. S.; Puri, V.; Ramanan, A.; Rajamannar, T.; Reddy, C. M.; Rodriguez-Hornedo, N.; Rogers, R. D.; Row, T. N. G.; Sanphui, P.; Shan, N.; Shete, G.; Singh, A.; Sun, C. C.; Swift, J. A.; Thaimattam, R.; Thakur, T. S.; Kumar Thaper, R.; Thomas, S. P.; Tothadi, S.; Vangala, V. R.; Variankaval, N.; Vishweshwar, P.; Weyna, D. R.; Zaworotko, M. J. Cryst. Growth. Des. 2012, 12, 2147. doi: 10.1021/cg3002948
[37]	Yan, D.-P. Chem. Eur. J. 2015, 21, 4880. doi: 10.1002/chem.201405456
[38]	Zhu, W.-G.; Wang, Y.-L.; Huang, C.-C.; Zhu, L.-Y.; Zhen, Y.-G.; Dong, H.-L.; Wei, Z.-X.; Guo, D.; Hu, W.-P. Sci. China Mater. 2020, 64, 169. doi: 10.1007/s40843-020-1372-6
[39]	Zhou, B.; Zhao, Q.-H.; Tang, L.-C.; Yan, D.-P. Chem. Commun. 2020, 56, 7698. doi: 10.1039/D0CC02730H
[40]	Zhu, W.-G.; Yi, Y.-P.; Zhen, Y.-G.; Hu, W.-P. Small. 2015, 11, 2150. doi: 10.1002/smll.201402330
[41]	Wang, Y.; Zhu, W.-G.; Du, W.-N.; Liu, X.-F.; Zhang, X.-T.; Dong, H.-L.; Hu, W.-P. Angew. Chem., Int. Ed. 2018, 57, 3963. doi: 10.1002/anie.201712949 pmid: 29442430
[42]	Wiscons, R. A.; Goud, N. R.; Damron, J. T.; Matzger, A. J. Angew. Chem., Int. Ed. 2018, 57, 9044. doi: 10.1002/anie.201805071 pmid: 29786921
[43]	Zhang, H.; Jiang, L.; Zhen, Y.; Zhang, J.; Han, G.; Zhang, X.; Fu, X.; Yi, Y.; Xu, W.; Dong, H.; Chen, W.; Hu, W.; Zhu, D. Adv. Electron. Mater. 2016, 2, 1500423. doi: 10.1002/aelm.201500423
[44]	Qin, Y.; Zhang, J.; Zheng, X.; Geng, H.; Zhao, G.; Xu, W.; Hu, W.; Shuai, Z.; Zhu, D. Adv. Mater. 2014, 26, 4093. doi: 10.1002/adma.201400056
[45]	Zhu, W.-G.; Dong, H.-L.; Zhen, Y.-G.; Hu, W.-P. Sci. China Mater. 2015, 58, 854. doi: 10.1007/s40843-015-0099-1
[46]	Wuest, J. D. Nat. Chem. 2012, 4, 74. doi: 10.1038/nchem.1256
[47]	Sun, L.-J.; Zhu, W.-G.; Yang, F.-X.; Li, B.; Ren, X.; Zhang, X.-T.; Hu, W.-P. Phys. Chem. Chem. Phys. 2018, 20, 6009. doi: 10.1039/C7CP07167A
[48]	Shi, S.; Chen, G. Nonlinear Optics. Xidian University, Xi'an, 2012, p. 2.
[49]	Chen, W.; Zhang, F.; Wang, C.; Jia, M.; Zhao, X.; Liu, Z.; Ge, Y.; Zhang, Y.; Zhang, H. Adv. Mater. 2021, 33, e2004446.
[50]	Bosshard, C.; Knöpfle, G.; Prêtre, P.; Günter, P. J. Appl. Phys. 1992, 71, 1594. doi: 10.1063/1.351237
[51]	Zhan, C.; Wang, D. Acta Phys.-Chim. Sin. 1999, 15, 805. (in Chinese) doi: 10.3866/PKU.WHXB19990907
	(詹传郎, 王夺元, 物理化学学报, 1999, 15, 805.)
[52]	Qian, Y.; Sun, Y.-M.; Liu, J.-Z. Acta Chim. Sinica. 1998, 56, 340. (in Chinese)
	(钱鹰, 孙岳明, 刘举正, 化学学报, 1998, 56, 340.)
[53]	Clays, K.; Persoons, A. Phys. Rev. Lett. 1991, 66, 2980. pmid: 10043668
[54]	Meng, F.-Q.; Fang, C.-S.; Cui, Y.-P.; Wang, X. Acta Chim. Sinica. 2000, 58, 384. (in Chinese)
	(孟凡青, 房昌水, 崔一平, 汪昕, 化学学报, 2000, 58, 384.)
[55]	Meredith, G.; David, J. Macromolecules. 1982, 15, 1385. doi: 10.1021/ma00233a033
[56]	Shi, W. Solid State Commun. 2000, 113, 483. doi: 10.1016/S0038-1098(99)00530-X
[57]	Shi, W. Opt. Commun. 2000, 183, 299. doi: 10.1016/S0030-4018(00)00855-5
[58]	Won, D.-S.; Jung, W.-T.; Lee, J.-Y. Polym. Bull. 2009, 62, 433. doi: 10.1007/s00289-008-0036-5
[59]	Muggli, D. J. Biomed. Mater. Res. 1999, 46, 271. doi: 10.1002/(SICI)1097-4636(199908)46:2＜271::AID-JBM17＞3.0.CO;2-X
[60]	Li, Y.; Li, H. Chinese Journal of Lasers. 2009, 36, 2140. (in Chinese) doi: 10.3788/CJL20093608.2140
	(李云, 李慧, 中国激光, 2009, 36, 2140.)
[61]	Charra, F.; Devaux, F.; Nunzi, J. M.; Raimond, P. Phys. Rev. Lett. 1992, 68, 2440. pmid: 10045398
[62]	Jia, Y.-J.; Guo, B.; Wang, G.-M. High Power Laser and Particle Beams. 2005, 17, 193. (in Chinese)
	(贾亚杰, 郭斌, 王恭明, 强激光与粒子束, 2005, 17, 193.)
[63]	Koscien, E.; Sanetra, J.; Gondek, E.; Jarosz, B.; Kityk, I. V.; Ebothe, J.; Kityk, A. V. Spectrochim. Acta A Mol. Biomol. 2005, 61, 1933.
[64]	Wang, L.-T.; Cui, Y.-P. Optoelectronic Technology. 2007, 27, 231. (in Chinese)
	(王良涛, 崔一平, 光电子技术, 2007, 27, 231.)
[65]	Sun, Y.-X.; Wang, W.-J. Journal of Jinggangshan University. 2011, 32, 33. (in Chinese)
	(孙彦星, 王文军, 井冈山大学学报, 2011, 32, 33.)
[66]	Boterashvili, M.; Lahav, M.; Shankar, S.; Facchetti, A.; van der Boom, M. E. J. Am. Chem. Soc. 2014, 136, 11926. doi: 10.1021/ja5066587 pmid: 25090376
[67]	Wang, Y.; Sun, L.-J.; Wang, C.; Yang, F.-X.; Ren, X.-C.; Zhang, X.-T.; Dong, H.-L.; Hu, W.-P. Chem. Soc. Rev. 2019, 48, 1492. doi: 10.1039/c8cs00406d pmid: 30283937
[68]	Erdelyi, M. Chem. Soc. Rev. 2012, 41, 3547. doi: 10.1039/c2cs15292d
[69]	Aakeröy, C. B.; Wijethunga, T. K.; Desper, J.; Đaković, M. Cryst. Growth. Des. 2016, 16, 2662. doi: 10.1021/acs.cgd.5b01770
[70]	Carletta, A.; Spinelli, F.; d'Agostino, S.; Ventura, B.; Chierotti, M. R.; Gobetto, R.; Wouters, J.; Grepioni, F. Chemistry. 2017, 23, 5317.
[71]	Riley, K. E.; Murray, J. S.; Fanfrlik, J.; Rezac, J.; Sola, R. J.; Concha, M. C.; Ramos, F. M.; Politzer, P. J. Mol. Model. 2011, 17, 3309. doi: 10.1007/s00894-011-1015-6
[72]	Zhu, W.-G.; Zheng, R.-H.; Zhen, Y.-G.; Yu, Z.-Y.; Dong, H.-L.; Fu, H.-B.; Shi, Q.; Hu, W.-P. J. Am. Chem. Soc. 2015, 137, 11038. doi: 10.1021/jacs.5b05586
[73]	Li, A.; Wang, J.; Liu, Y.; Xu, S.; Chu, N.; Geng, Y.; Li, B.; Xu, B.; Cui, H.; Xu, W. Phys. Chem. Chem. Phys. 2018, 20, 30297. doi: 10.1039/C8CP06363J
[74]	Arunan, E.; Desiraju, G. R.; Klein, R. A.; Sadlej, J.; Scheiner, S.; Alkorta, I.; Clary, D. C.; Crabtree, R. H.; Dannenberg, J. J.; Hobza, P.; Kjaergaard, H. G.; Legon, A. C.; Mennucci, B.; Nesbitt, D. J. Pure Appl. Chem. 2011, 83, 1619. doi: 10.1351/PAC-REP-10-01-01
[75]	Fan, G.; Yang, X.; Liang, R.; Zhao, J.; Li, S.; Yan, D.-P. CrystEngComm. 2016, 18, 240. doi: 10.1039/C5CE02019K
[76]	Yan, D.-P.; Delori, A.; Lloyd, G. O.; Friscic, T.; Day, G. M.; Jones, W.; Lu, J.; Wei, M.; Evans, D. G.; Duan, X. Angew. Chem., Int. Ed. 2011, 50, 12483. doi: 10.1002/anie.201106391
[77]	Zhang, J.-R.; Yan, J.; Xing, X.-Y.; Zhao, G.-J. SmartMat. 2021, 2, 554. doi: 10.1002/smm2.1054
[78]	Li, S.; Yan, D. Adv. Opt. Mater. 2018, 6, 1800445. doi: 10.1002/adom.201800445
[79]	Li, S.; Lin, Y.; Yan, D.-P. J. Mater. Chem. C. 2016, 4, 2527. doi: 10.1039/C6TC00067C
[80]	Thakuria, R.; Nath, N. K.; Saha, B. K. Cryst. Growth Des. 2019, 19, 523. doi: 10.1021/acs.cgd.8b01630
[81]	Ostroverkhova, O. Chem Rev. 2016, 116, 13279. pmid: 27723323
[82]	Khan, A.; Wang, M.; Usman, R.; Sun, H.; Du, M.; Xu, C. Cryst. Growth Des. 2017, 17, 1251. doi: 10.1021/acs.cgd.6b01636
[83]	Harada, J.; Ohtani, M.; Takahashi, Y.; Inabe, T. J. Am. Chem. Soc. 2015, 137, 4477. doi: 10.1021/jacs.5b00412 pmid: 25781627
[84]	Wang, Y.; Zhu, W.-G.; Dong, H.-L.; Zhang, X.-T.; Li, R.; Hu, W.-P. Top. Curr. Chem. (Cham). 2016, 374, 83.
[85]	Park, S. K.; Cho, I.; Gierschner, J.; Kim, J. H.; Kim, J. H.; Kwon, J. E.; Kwon, O. K.; Whang, D. R.; Park, J. H.; An, B. K.; Park, S. Y. Angew. Chem., Int. Ed. 2016, 55, 203. doi: 10.1002/anie.201508210
[86]	Zhou, Q.; Du, H.; Yu, Y.; Liu, C.; Li, J.; Ren, J.; Ji, Z.; Pang, Z. J. Phys. Chem. C. 2022, 126, 13381. doi: 10.1021/acs.jpcc.2c02726
[87]	Beerepoot, M. T.; Friese, D. H.; Ruud, K. Phys. Chem. Chem. Phys. 2014, 16, 5958. doi: 10.1039/c3cp55205e pmid: 24549316
[88]	Gotoh, T.; Kondoh, T.; Egawa, K. J. Opt. Soc. Am. B. 2020, 6, 703. doi: 10.1364/JOSAB.6.000703
[89]	Ji, Y.; Jones, C.; Baek, Y.; Park, G. K.; Kashiwagi, S.; Choi, H. S. Adv. Drug Deliv. Rev. 2020, 167, 121. doi: 10.1016/j.addr.2020.06.012
[90]	Jalani, G.; Naccache, R.; Rosenzweig, D. H.; Haglund, L.; Vetrone, F.; Cerruti, M. J. Am. Chem. Soc. 2016, 138, 1078. doi: 10.1021/jacs.5b12357
[91]	Kim, H. M.; Cho, B. R. Chem. Rev. 2015, 115, 5014. doi: 10.1021/cr5004425
[92]	Sun, C.-L.; Li, J.; Wang, X.-Z.; Shen, R.; Liu, S.; Jiang, J.-Q.; Li, T.; Song, Q.-W.; Liao, Q.; Fu, H.-B.; Yao, J.-N.; Zhang, H.-L. Chem. 2019, 5, 600. doi: 10.1016/j.chempr.2018.12.001
[93]	Shao, B.; Baroncini, M.; Qian, H.; Bussotti, L.; Di Donato, M.; Credi, A.; Aprahamian, I. J. Am. Chem. Soc. 2018, 140, 12323. doi: 10.1021/jacs.8b07108
[94]	Wang, Y.; Wu, H.; Li, P.; Chen, S.; Jones, L. O.; Mosquera, M. A.; Zhang, L.; Cai, K.; Chen, H.; Chen, X. Y.; Stern, C. L.; Wasielewski, M. R.; Ratner, M. A.; Schatz, G. C.; Stoddart, J. F. Nat. Commun. 2020, 11, 4633. doi: 10.1038/s41467-020-18431-7 pmid: 32934231
[95]	Matsukawa, T.; Mineno, Y.; Odani, T.; Okada, S.; Taniuchi, T.; Nakanishi, H. J. Cryst. Growth. 2007, 299, 344. doi: 10.1016/j.jcrysgro.2006.11.303
[96]	Wang, Y.; Zhang, X.; Zhang, X.; Zhou, T.; Cui, Z.; Zhang, K. J. Mater. Chem. A. 2022, 10, 1780. doi: 10.1039/D1TA09396G
[97]	Kim, S. J.; Kang, B. J.; Puc, U.; Kim, W. T.; Jazbinsek, M.; Rotermund, F.; Kwon, O. P. Adv. Opt. Mater. 2021, 9, 2101019. doi: 10.1002/adom.202101019
[98]	Shin, M. H.; Lee, S. H.; Kang, B. J.; Jazbinšek, M.; Yoon, W.; Yun, H.; Rotermund, F.; Kwon, O. P. Adv. Funct. Mater. 2018, 28, 1805257. doi: 10.1002/adfm.201805257
[99]	Kobayashi, H. Chem. Rev. 2010, 110, 2620. doi: 10.1021/cr900263j pmid: 20000749
[100]	Watt, W. W. Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 7075. doi: 10.1073/pnas.0832308100
[101]	Helmchen, F.; Denk, W. Nat. Methods. 2005, 2, 932. pmid: 16299478
[102]	Kim, H. M.; An, M. J.; Hong, J. H.; Jeong, B. H.; Kwon, O.; Hyon, J.-Y.; Hong, S.-C.; Lee, K. J.; Cho, B. R. Angew. Chem., Int. Ed. 2008, 47, 2231. doi: 10.1002/anie.200704586
[103]	Yang, W.; Chan, P. S.; Chan, M. S.; Li, K. F.; Lo, P. K.; Mak, N. K.; Cheah, K. W.; Wong, M. S. Chem. Commun. (Camb). 2013, 49, 3428. doi: 10.1039/c3cc41240g
[104]	Kim, M. K.; Lim, C. S.; Hong, J. T.; Han, J. H.; Jang, H. Y.; Kim, H. M.; Cho, B. R. Angew. Chem., Int. Ed. 2010, 49, 364.
[105]	Charier, S.; Ruel, O.; Baudin, J. B.; Alcor, D.; Allemand, J. F.; Meglio, A.; Jullien, L. Angew. Chem., Int. Ed. 2004, 43, 4785. doi: 10.1002/anie.200460557
[106]	Tian, Y. S.; Lee, H. Y.; Lim, C. S.; Park, J.; Kim, H. M.; Shin, Y. N.; Kim, E. S.; Jeon, H. J.; Park, S. B.; Cho, B. R. Angew. Chem., Int. Ed. 2009, 48, 8027. doi: 10.1002/anie.200901175
[107]	Feng, X.; Wang, M. Org. Lett. 2010, 12, 2194. doi: 10.1021/ol100474b
[108]	Kang, D. E.; Lim, C. S.; Kim, J. Y.; Kim, E. S.; Chun, H. J.; Cho, B. R. Anal. Chem. 2014, 86, 5353. doi: 10.1021/ac500329k
[109]	Park, H. J.; Lim, C. S.; Kim, E. S.; Han, J. H.; Lee, T. H.; Chun, H. J.; Cho, B. R. Angew. Chem., Int. Ed. 2012, 51, 2673. doi: 10.1002/anie.201109052
[110]	Ouyang, X.; Zeng, H.; Ji, W. J. Phys. Chem. B. 2009, 113, 14565. doi: 10.1021/jp905390q
[111]	Albota, M.; Beljonne, D.; Bredas, J.-L. Science. 1998, 281, 1653. doi: 10.1126/science.281.5383.1653 pmid: 9733507
[112]	Su, X.; Guang, S.; Li, C.; Xu, H.; Liu, X.; Wang, X.; Song, Y. Macromolecules. 2010, 43, 2840. doi: 10.1021/ma902789g
[113]	Pang, X.; Tao, Y.-L.; Zhang, J.-F.; Ren, G.-J. J. Mol. Struct. 2023, 1271, 134079. doi: 10.1016/j.molstruc.2022.134079
[114]	Yan, Z.; Guang, S.; Xu, H.; Liu, X.-Y. Dyes Pigments. 2013, 99, 720. doi: 10.1016/j.dyepig.2013.07.007
[115]	Hou, X.; Sun, J.; Liu, Z.; Yan, C.; Song, W.; Zhang, H. L.; Zhou, S.; Shao, X. Chem. Commun. (Camb). 2018, 54, 10981. doi: 10.1039/C8CC05480K
[116]	Naoto, S.; Atsushi, H. Chem. Mater. 2005, 17, 20. doi: 10.1021/cm0490165

有机共晶非线性光学材料及应用研究进展

Research Progress on Organic Cocrystals Nonlinear Optics Materials and Applications

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