Research Progress on Organic Cocrystals Nonlinear Optics Materials and Applications

doi:10.6023/A22100411

Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (2): 191-206.DOI: 10.6023/A22100411 Previous Articles Next Articles

Review

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)

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

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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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Fig. & Tab. 13

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

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

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]

Table 1. Representative examples of organic nonlinear optics cocrystal material

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

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

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

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

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

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

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

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

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

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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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