向列相液晶分子结构与黏度关系研究及BPNN-QSAR模型建立

陈红梅; 李世伟; 李凯靖; 张智勇; 陈浩; 王婷婷

doi:10.7498/aps.73.20231763

摘要

用于光学、微波通信调谐等器件的向列相液晶材料需要具备高响应速度来实现应用需求. 液晶器件响应速度与液晶的旋转黏度、液晶的双折射率等因素相关. 微波器件用向列相液晶, 常采用大π-电子共轭体系、大极性基团来提高液晶分子的双折射率和介电各向异性, 实现宽相位调制量, 也因此增大了液晶材料黏度, 影响了微波器件的响应速度. 本文以液晶黏度因素为主线, 对本课题组设计合成的42种向列相液晶在25 ℃时的黏度用旋转流变仪进行测试, 从液晶化合物的结构角度分析影响液晶黏度的因素. 首次建立向列相液晶分子结构与黏度的BPNN-QSAR定量构效模型, 模型测试组预测值跟真实值之间的相关系数q² = 0.607 > 0.5, 说明模型可用于液晶化合物的黏度性能预测, 并对影响黏度性能的分子结构描述符进行了探讨. 从实际应用出发结合本课题研究, 设计了两个系列7个大双折射率液晶分子, BPNN模型测试黏度量度小于同类型分子, 实验测试值与模型测试值相近.

关键词:

Abstract

Nematic liquid crystal materials designed for optics, microwave communication tuning, etc. need high response speed, which is related to the rotational viscosity and the birefringent index of the liquid crystal. In order to achieve a wide tuning range of phase modulation, the nematic liquid crystals often employ large π-electron conjugated systems and large polar groups to enhance the birefringence and dielectric anisotropy of the liquid crystal molecule, which, however, increases the viscosity of the liquid crystal material, deteriorating the response speed of the microwave device. Herein, we explore the viscosity of the nematic liquid crystal from the perspective of liquid crystal compound structure by testing the viscosity of our designed and synthesized forty-two different nematic liquid crystals by using a rotating rheometer at 25 ℃. To the best of our knowledge, the BPNN-QSAR quantitative structure-activity model between nematic liquid crystal molecular structure and viscosity is established for the first time. The correlation coefficient between the predicted value and the experimental value is q² = 0.607 > 0.5, indicating that the model can be used to predict the viscosity performances of liquid crystal compounds. Besides, the molecular structure descriptors affecting the viscosity properties are explored. Based on the practical application and this model, seven liquid crystal molecules of two series with large birefringent index are designed and tested. The viscosity predicted by the BPNN model is smaller than that of the molecules of the same type and matches with the measured viscosity.

Keywords:

nematic liquid crystal /
viscosity /
molecular structure /
quantitative structure-activity relationship

作者及机构信息

武汉轻工大学化学与环境工程学院, 武汉　430023

通信作者: 王婷婷, 1125364902@qq.com

基金项目: 国家装发部预研基金(批准号: 61409230701)资助的课题.

Authors and contacts

School of Chemical and Environmental Engineering, Wuhan Polytechnic University, Wuhan 430023, China

Corresponding author: Wang Ting-Ting, 1125364902@qq.com

Funds: Project supported by the National Equipment Development Department Pre-research Fund (Grant No. 61409230701).

文章全文 : translate this paragraph

参考文献

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施引文献

图 1 黏度量度VM 的试验值与预测值

Fig. 1. Experimental and predicted values of VM.

下载: 全尺寸图片幻灯片

图 2 两组同系物液晶分子的黏度量度VM和Shadow-Xlength与Num-RotatableBonds数值

Fig. 2. Shadow-Xlength, Num-RotatableBonds and VM for two groups of liquid crystal compounds.

下载: 全尺寸图片幻灯片

表 1 液晶化合物相变温度及25 ℃测试黏度值

Table 1. Phase transition temperature and 25 ℃ test viscosity value of liquid crystal compounds.

序号	化合物	分子结构	分子量/(g·mol^–1)	混晶黏度η/ (mPa·s^–1)	相变温度T/℃
1	3CC2		236.25	19.647	Cr –8.3 N 93.0 Iso
2	3CC4		264.28	20.983	Cr –10.9 N 66.8 Iso
3	5CPF		248.19	23.914	Liquid
4	3CPO1		232.18	21.619	Cr 32.0 Iso
5	5PP1		238.17	22.624	Cr 48.0 Iso
6	3GPS		271.08	24.313	Cr 45.0 Iso
7	2CPUS		357.14	23.961	Cr 50.0 N 175.0 Iso
8	5CPUS		399.18	24.874	Cr 50.5 N 196.3 Iso
9	3PGUF		344.12	24.694	Cr 62.5 Iso
10	5PGUF		372.15	25.021	Cr 56.4 Iso
11	5PGUS		411.13	26.486	Cr 57.4 N 159.2 Iso
12	5CPGUF		454.23	25.983	Cr 62.23 S 70 N 215 Iso
13	5CPGUS		493.21	26.400	Cr 71.53 N 234.15 Iso
14	5PGUOCF3		438.14	26.242	Cr 47.4 N 69.3 Iso
15	5CPGUOCF3		520.22	26.558	Cr 58.10 S 82.6 N 230.35 Iso
16	4PGPUF		434.17	24.884	Cr 96.8 SmC 111.9 SmA 214.6 N 231.4 Iso
17	5PP(2)GIP4		478.30	26.865	Cr 53.55 S 72.65 N 109.84 Iso
18	3PUQUF		428.10	25.191	Cr 47.2 Iso
19	3PGUQUF		522.12	26.205	Cr 88 N 135 Iso
20	3CEPC3		370.29	21.039	Cr 116.7 N 205.9 Iso
21	2CEPPN		333.17	21.072	Cr 89.0 N 245.6 Iso
22	3CPEP3		364.24	22.042	Cr 100.7 N 202.9 Iso
23	3CPEGN		365.18	23.498	Cr 107.1 N 214.4 Iso
24	2PEPN		251.09	20.946	Cr 77.6 N 80.9 Iso
25	3PEPN		265.11	22.869	Cr 108.1 N 113.5 Iso 51.9 N
26	4PEPN		279.13	24.478	Cr 71.3 N 74.2 Iso
27	3PTGS		295.08	22.476	Cr 55.22 S 69.37 Iso
28	5PTGS		323.11	23.248	Cr 50.59 N 90.59 Iso
29	7PTGS		351.15	24.016	Cr 41.98 N 45.06 Iso
30	5PTPO2		292.18	21.512	Cr 65.6 N 95.3 Iso 88.3 N
31	5PTUS		341.1	22.577	Cr 43.99 Iso
32	5CPTUS		423.18	22.974	Cr 62 N 228 Iso
33	5PPTUS		417.14	23.809	Cr 55.0 S 119.0 N 208.5 Iso
34	4PUTGS		421.11	22.559	Cr 93 Iso
35	2PTPP3		360.17	22.768	Cr 73.5 N 186 Iso
36	3PTPP2		360.17	22.583	Cr 73 N 189 Iso
37	3PTPP4		388.20	23.682	Cr 66.1 S 88.0 N 169.5 Iso
38	4PTPP3		388.29	23.445	Cr 38.5 S 60.0 N 174.0 Iso
39	4PTGTP4		444.21	26.201	Cr 78 N 180 Iso
40	4PTGTP5		458.22	26.918	Cr 72.12 N 172.81 Iso
41	5PP(1)PUF		444.21	25.014	Cr 76.9 N 127.6 Iso
42	5PPI(1)PUF		444.21	24.608	Cr 77.4 N 134 Iso
43	5CB		249.15	25.010	Cr 24 N 35.3 Iso
注: Cr, 各向异性晶体相; S, 近晶相; N, 向列相; Iso, 各向同性; SmA, SmA相态; SmC, SmC相态.

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表 2 BPNN模型的结果

Table 2. Results of BPNN model.

网络结构	R²	R² (cross-validated)	q²
12-4-1	0.9238	0.5089	0.6070

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表 3 训练组与测试组液晶化合物的试验黏度量度及预测黏度量度

Table 3. VM_expt and VM_pred of liquid compounds in the training group and test group

No.	Compounds	η/(mPa·s)	$ {{\mathrm{VM}}}_{{\mathrm{expt}}} $	$ {{\mathrm{VM}}}_{{\mathrm{pred}}} $	$ \Delta {\mathrm{VM}} $	δ
1*	3CC2	19.647	1.293	1.319	0.026	0.020
2	3CC4	20.983	1.322	1.318	0.004	0.003
3	5CPF	23.914	1.379	1.376	0.002	0.002
4	3CPO1	21.619	1.335	1.336	0.001	0.001
5	5PP1	22.624	1.355	1.357	0.002	0.001
6	3GPS	24.313	1.386	1.363	0.023	0.017
7*	2CPUS	23.961	1.380	1.378	0.002	0.001
8	5CPUS	24.874	1.396	1.401	0.006	0.004
9	3PGUF	24.694	1.393	1.396	0.004	0.002
10*	5PGUF	25.021	1.398	1.405	0.006	0.004
11	5PGUS	26.486	1.423	1.425	0.002	0.001
12	5CPGUF	25.983	1.415	1.414	0.000	0.001
13	5CPGUS	26.400	1.422	1.418	0.004	0.003
14	5PGUOCF3	26.242	1.419	1.417	0.002	0.001
15	5CPGUOCF3	26.558	1.424	1.424	–0.001	0.000
16	4PGPUF	24.884	1.396	1.410	0.014	0.010
17	5PP(2)GIP4	26.865	1.429	1.426	0.003	0.002
18	3PUQUF	25.191	1.401	1.411	0.010	0.007
19	3PGUQUF	26.205	1.418	1.411	0.007	0.005
20	3CEPC3	21.039	1.323	1.326	0.003	0.002
21	2CEPPN	21.072	1.324	1.320	0.003	0.003
22	3CPEP3	22.042	1.343	1.344	0.001	0.001
23	3CPEGN	23.498	1.371	1.365	0.006	0.004
24	2PEPN	20.946	1.321	1.341	0.020	0.015
25*	3PEPN	22.869	1.359	1.353	0.006	0.004
26	4PEPN	24.478	1.389	1.365	0.024	0.017
27	3PTGS	22.476	1.352	1.347	0.005	0.004
28*	5PTGS	23.248	1.366	1.372	0.006	0.004
29	7PTGS	24.916	1.396	1.401	0.004	0.004
30	5PTPO2	21.512	1.333	1.337	0.004	0.003
31	5PTUS	22.577	1.354	1.364	0.011	0.007
32	5CPTUS	22.974	1.361	1.367	0.006	0.004
33*	5PPTUS	23.809	1.377	1.427	0.050	0.036
34	4PUTGS	22.559	1.353	1.364	0.011	0.008
35	2PTPP3	22.768	1.357	1.353	0.004	0.003
36	3PTPP2	22.583	1.354	1.345	0.009	0.007
37*	3PTPP4	23.682	1.374	1.374	-0.001	0.001
38	4PTPP3	23.445	1.370	1.366	0.004	0.003
39*	4PTGTP4	26.201	1.418	1.398	0.020	0.014
40	4PTGTP5	26.918	1.430	1.427	-0.003	0.002
41	5PP(1)PUF	25.014	1.398	1.412	0.014	0.010
42	5PPI(1)PUF	24.608	1.391	1.406	0.015	0.011
注: *为测试组数据.

下载: 导出CSV

表 4 结构描述符及相关分子结构信息、对应敏感度

Table 4. Structural descriptors and related molecular structure information, and corresponding sensitivity.

描述符	结构信息	敏感度
ES-Count-aasC	代表具有两个芳香键和一个单键的碳的电拓扑状态 (Electrotopological State, Estate)和电子结构信息	0.999735
Dipole-X	指示静电场中分子的强度和取向行为的3D电子描述符	0.947414
Num-RotatableBonds	可旋转键, 定义为既不在环中又不在末端的重原子之间的单键, 即连接到仅与氢相连的重原子. 作为一种特殊情况, 酰胺C—N键是不可旋转的	0.814023
Shadow-Xlength	阴影X长度, 表征分子形状的一组几何描述符, 代表分子在x维度上的长度	0.307771
ES-Sum-sssCH	计算具有三个单键的CH的电拓扑状态(Estate)总和	0.208536
JX	Balaban指数	0.118169
ES-Count-tsC	代表具有一个三键的碳的电拓扑状态(Estate)计数	–0.707114
ES-Count-ssCH₂	代表具有两个单键的CH₂的电拓扑状态(Estate)计数	–0.671564
Wiener	维纳指数, 代表分子中所有重原子对之间存在的化学键的总和	–0.653192
ES-Sum-sF	计算F原子的电拓扑状态(Estate)	–0.400111
ES-Count-sF	F原子的电拓扑状态(Estate)计数	–0.400111
ALogP	使用Ghose和Crippen发表的基于原子的方法计算辛醇-水分配系(LogP)	–0.128786
注: ES-Sum-xxx: 某原子电子结构和拓扑结构计算总和; ES-Count-xxx: 某种类型的原子在分子中出现的数目; -xxx中s, 单键; d, 双键; t, 三键; a, 芳香键^[38,39].

下载: 导出CSV

[1]	Demus D, Goodbye J W, Gray G W 1998 Handbook of Liquid Crystals Chichester (Wiley-VCH) p237
[2]	杨傅子 2008 物理学进展 28 107 Google Scholar Yang F Z 2008 Prog. Phys. 28 107 Google Scholar
[3]	曹召良, 穆全全, 胡立发 2008 液晶与显示 23 157 Google Scholar Cao Z L, Mu Q Q, Hu L F 2008 Liq. Cryst. Disp. 23 157 Google Scholar
[4]	李潭, 王震, 张智勇 2017 液晶与显示 32 862 Google Scholar Li T, Wang Z, Zhang Z Y 2017 Liq. Cryst. Disp. 32 862 Google Scholar
[5]	Qiu L L, Zhu L, Xu Y 2020 IEEE T. Antenn. Progag. 685680 Google Scholar
[6]	Robert C, Zbigniew C, Yuriy G 2018 Liq. Cryst. Rev. 6 17 Google Scholar
[7]	Alihosseini F, Ahmadi V, Mir A 2015 Liq. Cryst. 42 1638 Google Scholar
[8]	Jiang D, Liu Y, Li X 2019 IEEE Access 7 126265 Google Scholar
[9]	Kundtz N 2014 Microwave 57 56
[10]	Nishikawa H, Shiroshita K, Higuchi H 2017 Adv. Mater. 29 1702354 Google Scholar
[11]	Mandle R J, Cowling S J, Goodby J W 2017 Phys. Chem. Chem. Phys. 19 11429 Google Scholar
[12]	Zhao X, Zhou J 2021 Proc. Natl. Acad. Sci. 118 21111 Google Scholar
[13]	赵秀虎, 黄明俊, Satoshiay A 2023 液晶与显示 38 77 Google Scholar Zhao X H, Huang M J, Satoshiay A 2023 Liq. Cryst. Disp. 38 77 Google Scholar
[14]	Li B X, Xiao R L, Paladugu S 2019 Opt. Express 27 3861 Google Scholar
[15]	杨槐, 王萌, 张兰英 2015 CN 106701105 B 9 Yang H, Wang M, Zhang L Y 2015 CN Patent 106701105 B 9
[16]	高鸿锦 2011 液晶化学 (北京: 清华大学出版社)第48页 Gao J H 2011 Liquid Crystals Chemistry (Beijing: Qinghua University Press) p48
[17]	Chen C Y, Tsai T R, Pan C L, Pan R P 2003 Appl. Phys. Lett. 83 4497 Google Scholar
[18]	Reuter M G K, Garbat K, Vieweg N, Fischer B N, Dąbrowski R, Koch M, Dziaduszek J, Urban S 2013 J. Mater. Chem. C 1 4457 Google Scholar
[19]	张智勇, 刘可庆, 戴志群 2014 液晶与显示 29 873 Google Scholar Zhang Z Y, Liu K Q, Dai Z Q 2014 Liq. Cryst. Disp. 29 873 Google Scholar
[20]	Herman J, Dziaduszek J, Dąbrowski R 2013 Liq. Cryst. 40 1174 Google Scholar
[21]	张然, 彭增辉, 刘永刚 2009 液晶与显示 6 789 Zhang R, Peng Z H, Liu Y G 2009 Liq. Cryst. Disp. 6 789
[22]	Bock F J, Kneppe H, Schneider F 1986 Liq. Cryst. 1 239 Google Scholar
[23]	Belyaev V V 1989 Russ. Chem. Rev. 58 917 Google Scholar
[24]	Gauza S, Jiao M, Wu S T 2008 Liq. Cryst. 35 1401 Google Scholar
[25]	Gauza S, Kula P, Liang X 2009 Mol. Cryst. Liq. Cryst. 509 47 Google Scholar
[26]	刘运, 张智勇, 任占冬 2010 液晶与显示 4 490 Google Scholar Liu Y, Zhang Z Y, Ren Z D 2010 Liq. Cryst. Disp. 4 490 Google Scholar
[27]	Deng M M, Wang Y, Zhang Z 2012 Chin. J. Chem. 29 1093 Google Scholar
[28]	Soltani T, Fouzai M, Dhaoudi H 2016 Phase Transi. 89 622 Google Scholar
[29]	Bulsara A R, Maren A J, Schmera G 1993 Biol. Cybern. 70 145 Google Scholar
[30]	袁永娜 2010 博士学位论文(兰州: 兰州大学) Yuan Y N 2010 Ph. D. Dissertation (Lanzhou: Lanzhou University
[31]	Hansch C, Steward A R 1964 J. Med. Chem. 7 691 Google Scholar
[32]	王婷婷, 戴康, 王展, 高新蕾 2014 华中师范大学学报 48 379 Google Scholar Wang T T, Dai K, Wang Z, Gao X L 2014 J. Central China Normal Univ. 48 379 Google Scholar
[33]	Dąbrowski R, Dziaduszek J, Ziółek A 2007 Opto-Electro. Rev. 15 47 Google Scholar
[34]	Li J, Hu M, Chen R 2021 J. Mol. Liq. 325 115236 Google Scholar
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