新型二氟乙烯端基异硫氰酸酯化合物的合成及性能

doi:10.7503/cjcu20170031

高等学校化学学报 ›› 2017, Vol. 38 ›› Issue (10): 1788.doi: 10.7503/cjcu20170031

新型二氟乙烯端基异硫氰酸酯化合物的合成及性能

李娟利^1,^2,³, 彭增辉³, 李建^1,², 胡明刚^1,², 安忠维^1,^2,⁴(), 张璐^1,²

1. 氟氮化工资源高效开发与利用国家重点实验室, 西安 710065
2. 西安近代化学研究所光电材料事业部, 西安 710065
3. 中国科学院长春光学精密机械与物理研究所, 应用光学国家重点实验室, 长春 130033
4. 陕西师范大学材料科学与工程学院, 西安 710119

收稿日期:2017-01-16 出版日期:2017-10-10 发布日期:2017-09-21
作者简介:联系人简介: 安忠维, 男, 博士, 教授, 博士生导师, 主要从事液晶材料研究. E-mail:gmecazw@163.com
基金资助:
国防基础科研项目(批准号: B0520132007, B1120132028)、陕西省科技攻关项目(批准号: 2016GY-212)、应用光学国家重点实验室开放基金(批准号: Y6133FQ112)和国家自然科学基金(批准号: 61378075)资助

Synthesis and Properties of Novel Isothiocyanatotolane Liquid Crystals with Terminal Difluorovinyl Substitute^†

LI Juanli^1,^2,³, PENG Zenghui³, LI Jian^1,², HU Minggang^1,², AN Zhongwei^1,^2,^4,^*(), ZHANG Lu^1,²

1. State Key Laboratory of Fluorine & Nitrogen Chemicals, Xi’an 710065, China
2. Optical and Electrical Materials Department, Xi’an Modern Chemistry Research Institute, Xi’an 710065, China
3. State Key Laboratory of Applied Optics, Changchun Institute of Optics, Fine Mechanics and Physics,Chinese Academy of Sciences, Changchun 130033, China
4. School of Materials Science and Engineering, Shaanxi Normal University, Xi’an 710119, China

Received:2017-01-16 Online:2017-10-10 Published:2017-09-21
Contact: AN Zhongwei E-mail:gmecazw@163.com
Supported by:
† Supported by the Defense Industrial Technology Development Program of China(Nos.B0520132007, B1120132028), the Key Science and Technology Program of Shaanxi Province, China(No.2016GY-212), the State Key Laboratory of Applied Optics, China(No.Y6133FQ112) and the National Natural Science Foundation of China(No.61378075)

摘要/Abstract

摘要：

以对碘苯甲醛和二氟氯乙酸钠为原料, 经5步反应合成了4个新型二氟乙烯端基异硫氰酸酯化合物, 经气相色谱(GC)检测纯度均大于98.7%, 总收率为23%~31%. 采用红外光谱(IR), 核磁共振波谱(NMR)和质谱(MS)等技术对化合物的结构进行了表征. 通过差示扫描量热(DSC)法和偏光显微镜(POM)研究了化合物的介晶性, 采用外推法得到了化合物的双折射率和旋转黏度值. 结果表明, 化合物A1~A3均呈现较宽的互变向列相; 用二氟乙烯基替代乙基后, 化合物的向列相拓宽了31~62 ℃, 双折射率提高了0.038~0.052, 旋转黏度降低. 基于新型二氟乙烯基异硫氰酸酯化合物的高双折射率混合液晶配方具有更宽的向列相温度范围、更高的双折射率、更低的旋转黏度及更高的品质因子.

关键词: 二氟乙烯基, 异硫氰酸酯, 向列相, 双折射率, 旋转黏度

Abstract:

Four kinds of new isothiocyanate liquid crystals composed of tolane core and difluorovinyl terminal group(A1—A4) were synthesized via five step reactions based on 4-iodobenzaldehyde, and four ethyl analogues B1—B4 as comparison structures were also prepared. The structure characterizations of all related pro-ducts were performed using infrared spectrometer(IR), ¹H-nuclear magnetic resonance(¹H NMR) and mass spectrometer(MS). The mesomorphic properties were investigated by differential scanning calorimeter(DSC) and hot stage polarizing optical microscope(HS-POM). The birefringence values and rotational viscosity were extrapolated. The results showed that the target compounds A1, A2 and A3 exhibit wider nematic phase range(31—62 ℃). Replacement of ethyl chain by difluorovinyl as terminal group is enabled to not only enlarge the nematic phase temperature range but also increase birefringence(Δn=0.038—0.052) and reduce rotational viscosity. The high birefringence mixtures based new liquid crystals with terminal difluorovinyl substitute have wider nematic phase range, higher birefringence, lower rotational viscosity and larger figure-of-merit(FoM).

Key words: Difluorovinyl, Isothiocyanate, Nematic phase, Birefringence, Rotational viscosity

中图分类号:

O625

TrendMD:

李娟利, 彭增辉, 李建, 胡明刚, 安忠维, 张璐. 新型二氟乙烯端基异硫氰酸酯化合物的合成及性能. 高等学校化学学报, 2017, 38(10): 1788.

LI Juanli, PENG Zenghui, LI Jian, HU Minggang, AN Zhongwei, ZHANG Lu. Synthesis and Properties of Novel Isothiocyanatotolane Liquid Crystals with Terminal Difluorovinyl Substitute^†. Chem. J. Chinese Universities, 2017, 38(10): 1788.

图/表 11

Fig.1 Target compounds(A) and the comparison structures(B)

Scheme 1 Synthesis of target compounds A1—A4

Table 1 Yields, appearances, melting points and MS data of the intermediates and target compounds

Compd.	Yield(%)	Appearance	m. p./℃	MS, m/z(RI,%)
1	75	Colourless liquid		266.1(M⁺, 100), 139.1(24), 119.1(41), 99.1(10), 63.1(7)
2a	78	Brown solid	101.6—102.8	117.0(M⁺, 100), 89.0(25), 63.0(5)
2b	56	Brown liquid		134.9(M⁺, 100), 107.0(17), 88.0(6), 67.5(3)
2c	68	Brown solid	45.1—46.0	135.0(M⁺, 100), 107.0(24), 81.0(3), 67.6(3)
2d	55	Brown solid	65.0—67.2	153.0(M⁺, 100), 125.0(11), 106.0(12), 76.4(3), 62.0(1)
3a	67	Brown solid	105.5—108.7	255.1(M⁺, 100), 207.0(5), 176.0(2), 127.6(11)
3b	65	Brown solid	90.5—93.4	273.1(M⁺, 100), 225.0(7), 136.6(11)
3c	50	Brown solid	101.8—104.5	273.0(M⁺, 100), 225.0(5), 136.5(7)
3d	31	Brown solid	88.0—89.5	291.0(M⁺, 100), 271.0(2), 243(5), 145.5(7)
A1	92	White solid	73.4—73.9	297.7(M⁺,100), 265.8(24), 238.7(41), 189.6(23), 148.9(55), 119.4(27)
A2	67	White solid	96.3—97.7	315.6(M⁺,100), 283.8(26), 256.7(36), 207.6(18), 158.0(61), 128.5(30)
A3	79	White solid	92.2—93.2	314.9(M⁺,100), 283.0(8), 256.0(14), 207.0(6),157.6(19)
A4	68	White solid	120.3—120.7	333.6(M⁺,100), 301.8(27), 274.7(35), 167.0(61), 137.4(23)

Table 2 1H NMR and IR data of the intermediates and target compounds

Compd.	¹H NMR(CDCl₃, 500 MHz), δ	IR(KBr), $ν ˙$ /cm^-1
1	5.18—5.24(q, 1H), 7.05—7.09(d, 2H, J=8.5 Hz), 7.64—7.66(m, 2H)	3038, 2926, 2307, 1900, 1729, 1675, 1489, 1400, 1355, 1249, 1169, 1006, 940, 839, 801, 704
2a	2.95(s, 1H), 3.81(s, 2H), 6.59—6.60(m, 2H), 7.29—7.30(m, 2H)	3486, 3388, 3037, 2918, 2609, 2250, 2096, 1619, 1513, 1305, 1201, 1177, 1050, 939, 829, 672
2b	2.51(s, 1H), 3.88(s, 2H), 6.68(s, 1H), 7.10—7.13(m, 2H)	3476, 3382, 3296, 3225, 2926, 2664, 2186, 2104, 1628, 1515, 1439, 1365, 1246, 1187, 1122, 941, 874, 819, 598
2c	3.18(s, 1H), 3.94(s, 2H), 6.34—6.38(m, 2H), 7.22—7.26(q, 1H)	3482, 3389, 3268, 2103, 2609, 1626, 1509, 1331, 1117, 957, 849, 742
Compd.	¹H NMR(CDCl₃, 500 MHz), δ	IR(KBr), ν˙/cm^-1
2d	2.90(s, 1H), 3.83(s, 2H), 6.86—6.93(m, 2H)	3479, 3392, 3287, 3073, 2982, 2925, 2112, 1732, 1643, 1580, 1526, 1337, 1262, 1099, 959, 859, 800, 716, 691
3a	3.83(s, 2H), 5.24—5.30(q, 1H), 6.26—6.64(q, 2H), 7.27—7.29(d, 2H, J=8.5 Hz), 7.33—7.34(q, 2H), 7.44—7.46(d, 2H, J=8.5 Hz)	3471, 3377, 3091, 3034, 2209, 1617, 1597, 1517, 832, 725, 671, 528
3b	3.90(s, 2H), 5.24—5.30(q, 1H), 6.70—6.73(t, 1H), 7.12—7.18(m, 2H), 7.28—7.30(d, 2H, J=8.0 Hz), 7.44—7.46(d, 2H, J=8.5 Hz)	3450, 3367, 3046, 2205, 1630, 1570, 1520, 834, 767, 607, 536
3c	3.94(s, 2H), 5.24—5.30(q, 1H), 6.38—6.41(t, 2H), 7.28—7.36(m, 3H), 7.44—7.51(m, 2H)	3501, 3406, 3094, 3032, 2207, 1626, 1605, 1523, 838, 741, 675, 605
3d	3.88(s, 2H), 5.25—5.31(q, 1H), 6.98—7.05(m, 2H), 7.29—7.31(d, 2H, J=8.5 Hz ), 7.44—7.46(d, 2H, J=8.5 Hz)	3449, 3329, 3072, 3045, 2213, 1642, 1578, 1525, 840, 720, 617, 536
A1	5.26—5.32(q, 1H), 7.19—7.21(d, 2H, J=8.5 Hz), 7.31—7.33(d, 2H, J=8.5 Hz), 7.49(t, 4H, J=16 Hz)	3078, 3032, 2202(C≡≡C), 2109(NCS), 1608, 1518, 942, 840, 806, 620
A2	5.26—5.33(q, 1H), 7.15(t, 1H), 7.26—7.33(m, 4H), 7.47—7.49(d, 2H, J=8.5 Hz)	3090, 3036, 2209(C≡≡C), 2048(NCS), 1602, 1514, 937, 845, 779
A3	5.26—5.32(q, 1H), 6.96—7.02(m, 2H), 7.31—7.33(d, 2H, J=8.5 Hz), 7.46—7.51(m, 3H)	3072, 3032, 2217(C≡≡C), 2106(NCS), 1613, 1515, 938, 867, 852, 605
A4	5.27—5.33(q, 1H), 7.09—7.13(m, 2H), 7.32—7.34(d, 2H, J=8.0 Hz), 7.47—7.48(m, 2H, J=8.5 Hz)	3096, 3033, 2214(C≡≡C), 2050(NCS), 1620, 1515, 941, 849, 706, 624

Table 2 1H NMR and IR data of the intermediates and target compounds

Compd.	¹H NMR(CDCl₃, 500 MHz), δ	IR(KBr), $ν ˙$ /cm^-1
1	5.18—5.24(q, 1H), 7.05—7.09(d, 2H, J=8.5 Hz), 7.64—7.66(m, 2H)	3038, 2926, 2307, 1900, 1729, 1675, 1489, 1400, 1355, 1249, 1169, 1006, 940, 839, 801, 704
2a	2.95(s, 1H), 3.81(s, 2H), 6.59—6.60(m, 2H), 7.29—7.30(m, 2H)	3486, 3388, 3037, 2918, 2609, 2250, 2096, 1619, 1513, 1305, 1201, 1177, 1050, 939, 829, 672
2b	2.51(s, 1H), 3.88(s, 2H), 6.68(s, 1H), 7.10—7.13(m, 2H)	3476, 3382, 3296, 3225, 2926, 2664, 2186, 2104, 1628, 1515, 1439, 1365, 1246, 1187, 1122, 941, 874, 819, 598
2c	3.18(s, 1H), 3.94(s, 2H), 6.34—6.38(m, 2H), 7.22—7.26(q, 1H)	3482, 3389, 3268, 2103, 2609, 1626, 1509, 1331, 1117, 957, 849, 742
Compd.	¹H NMR(CDCl₃, 500 MHz), δ	IR(KBr), ν˙/cm^-1
2d	2.90(s, 1H), 3.83(s, 2H), 6.86—6.93(m, 2H)	3479, 3392, 3287, 3073, 2982, 2925, 2112, 1732, 1643, 1580, 1526, 1337, 1262, 1099, 959, 859, 800, 716, 691
3a	3.83(s, 2H), 5.24—5.30(q, 1H), 6.26—6.64(q, 2H), 7.27—7.29(d, 2H, J=8.5 Hz), 7.33—7.34(q, 2H), 7.44—7.46(d, 2H, J=8.5 Hz)	3471, 3377, 3091, 3034, 2209, 1617, 1597, 1517, 832, 725, 671, 528
3b	3.90(s, 2H), 5.24—5.30(q, 1H), 6.70—6.73(t, 1H), 7.12—7.18(m, 2H), 7.28—7.30(d, 2H, J=8.0 Hz), 7.44—7.46(d, 2H, J=8.5 Hz)	3450, 3367, 3046, 2205, 1630, 1570, 1520, 834, 767, 607, 536
3c	3.94(s, 2H), 5.24—5.30(q, 1H), 6.38—6.41(t, 2H), 7.28—7.36(m, 3H), 7.44—7.51(m, 2H)	3501, 3406, 3094, 3032, 2207, 1626, 1605, 1523, 838, 741, 675, 605
3d	3.88(s, 2H), 5.25—5.31(q, 1H), 6.98—7.05(m, 2H), 7.29—7.31(d, 2H, J=8.5 Hz ), 7.44—7.46(d, 2H, J=8.5 Hz)	3449, 3329, 3072, 3045, 2213, 1642, 1578, 1525, 840, 720, 617, 536
A1	5.26—5.32(q, 1H), 7.19—7.21(d, 2H, J=8.5 Hz), 7.31—7.33(d, 2H, J=8.5 Hz), 7.49(t, 4H, J=16 Hz)	3078, 3032, 2202(C≡≡C), 2109(NCS), 1608, 1518, 942, 840, 806, 620
A2	5.26—5.33(q, 1H), 7.15(t, 1H), 7.26—7.33(m, 4H), 7.47—7.49(d, 2H, J=8.5 Hz)	3090, 3036, 2209(C≡≡C), 2048(NCS), 1602, 1514, 937, 845, 779
A3	5.26—5.32(q, 1H), 6.96—7.02(m, 2H), 7.31—7.33(d, 2H, J=8.5 Hz), 7.46—7.51(m, 3H)	3072, 3032, 2217(C≡≡C), 2106(NCS), 1613, 1515, 938, 867, 852, 605
A4	5.27—5.33(q, 1H), 7.09—7.13(m, 2H), 7.32—7.34(d, 2H, J=8.0 Hz), 7.47—7.48(m, 2H, J=8.5 Hz)	3096, 3033, 2214(C≡≡C), 2050(NCS), 1620, 1515, 941, 849, 706, 624

Table 3 Effect of different substrates on the reaction

Substrate	n(Target product):n(Raw material)
4-[(3-Fluoro-4-isthiocyanatophenyl)ethynyl]benzaldehyde	0:100
4-Ethynylbenzadehyde	63:24
4-Bromobenzaldehyde	64:24
4-Iodobenzaldehyde	85:12

Table 4 Phase transition temperature and enthalpy change of compounds A1—A4 and B1—B4*

Compd.	Transition temperature/℃		Enthalpy change/(kJ·mol^-1)
	Heating process	Cooling process	Heating process		Cooling process
	Heating process	Cooling process	Melting enthalpy	Clearing enthalpy	Melting enthalpy	Clearing enthalpy
A1	Cr 73.39 N 135.29 I	I 134.00 N 68.64 Cr	25.11	0.49	-0.40	-12.10
A2	Cr 96.28 N 127.65 I	I 126.75 N 89.67 Cr	27.92	0.32	-0.42	-26.86
A3	Cr 92.21 N 132.64 I	I 110.69 N 84.33 Cr	26.62	0.38	-0.02	-19.80
A4	Cr 120.29 I	I 108.03 Cr	32.03		-27.35
B1	Cr 94.58 I	I 89.56 Cr	25.07		-15.37
B2	Cr 70.76 I	I 44.93 Cr	23.83		-16.21
B3	Cr 73.86 I	I 50.00 Cr	26.65		-25.21
B4	Cr 81.87 I	I 63.99 Cr	15.08		-16.87

Fig.2 POM images of compounds A2 and A3 during heating process(200×) Nematic schlieren texture of A2 at 102.1 ℃(A) and A3 at 100.5 ℃(B), respectively.

Fig.3 Effect of lateral fluorine substituent on the thermal properties of target compounds A1—A4

Table 5 Physical properties of the mixtures

Mixture or compd.	Δε	γ₁/(mPa·s)	Δn(589 nm)	Mixture or compd.	Δε	γ₁/(mPa·s)	Δn(589 nm)
P0	5.63	156.5	0.080	A1	5.23	1.83	0.483
A1+P0	5.61	125.3	0.1002	A2	9.63	4.40	0.478
A2+P0	5.83	130.9	0.0999	A3	6.03	4.46	0.474
A3+P0	5.65	131.0	0.0997	A4	10.83	2.25	0.442
A4+P0	5.89	126.6	0.0981	B1	16.83	5.43	0.442
B1+P0	6.19	132.3	0.0986	B2	21.23	5.12	0.428
B2+P0	6.41	131.9	0.0974	B3	10.03	2.33	0.436
B3+P0	5.85	126.8	0.0978	B4	26.23	4.97	0.390
B4+P0	6.66	131.7	0.0955

Table 6 Calculated and measured birefringence of the investigated compounds

Compd.	α_XX/a.u.	A_YY/a.u.	α_ZZ/a.u.	Δα/a.u.	$α ?$ /a.u.	Δn
A1	561.68	182.26	27.67	456.71	257.21	0.4707
B1	499.02	167.39	41.05	394.80	235.82	0.4606
A2	573.76	181.83	27.81	468.94	261.13	0.4552
B2	511.26	166.88	41.19	407.23	239.78	0.4439
A3	568.17	185.07	27.75	461.76	260.33	0.4483
B3	504.46	169.34	40.83	399.37	238.21	0.4354

Table 6 Calculated and measured birefringence of the investigated compounds

Compd.	α_XX/a.u.	A_YY/a.u.	α_ZZ/a.u.	Δα/a.u.	$α ?$ /a.u.	Δn
A1	561.68	182.26	27.67	456.71	257.21	0.4707
B1	499.02	167.39	41.05	394.80	235.82	0.4606
A2	573.76	181.83	27.81	468.94	261.13	0.4552
B2	511.26	166.88	41.19	407.23	239.78	0.4439
A3	568.17	185.07	27.75	461.76	260.33	0.4483
B3	504.46	169.34	40.83	399.37	238.21	0.4354

Table 7 Physical properties of the mixtures

Mixture	Composition	$T mp a$ /℃	$T b ni$ /℃	Δn(25 ℃, 589 nm)	γ₁/ $K c 11$ /(ms·m^-2)	FoM^d/(m²·s^-1)
Mix1-A	Host 1+8%A1+8%A2	-17.72	106.05	0.4179	11.71	14.9
Mix1-B	Host 1+8%B1+8%B2	-16.81	88.96	0.3935	13.07	11.8
Mix2-A	Host 2+6%A1+6%A2	<-40	81.66	0.3797	10.84	13.3
Mix2-B	Host 2+6%B1+6%B2	<-40	67.24	0.3559	11.26	11.2

Table 7 Physical properties of the mixtures

Mixture	Composition	$T mp a$ /℃	$T b ni$ /℃	Δn(25 ℃, 589 nm)	γ₁/ $K c 11$ /(ms·m^-2)	FoM^d/(m²·s^-1)
Mix1-A	Host 1+8%A1+8%A2	-17.72	106.05	0.4179	11.71	14.9
Mix1-B	Host 1+8%B1+8%B2	-16.81	88.96	0.3935	13.07	11.8
Mix2-A	Host 2+6%A1+6%A2	<-40	81.66	0.3797	10.84	13.3
Mix2-B	Host 2+6%B1+6%B2	<-40	67.24	0.3559	11.26	11.2

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新型二氟乙烯端基异硫氰酸酯化合物的合成及性能

Synthesis and Properties of Novel Isothiocyanatotolane Liquid Crystals with Terminal Difluorovinyl Substitute^†

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新型二氟乙烯端基异硫氰酸酯化合物的合成及性能

Synthesis and Properties of Novel Isothiocyanatotolane Liquid Crystals with Terminal Difluorovinyl Substitute†

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Synthesis and Properties of Novel Isothiocyanatotolane Liquid Crystals with Terminal Difluorovinyl Substitute^†