含乙撑桥键二苯炔四环液晶的合成及性能

doi:10.7503/cjcu20131233

高等学校化学学报 ›› 2014, Vol. 35 ›› Issue (7): 1433.doi: 10.7503/cjcu20131233

含乙撑桥键二苯炔四环液晶的合成及性能

陈然¹, 安忠维^1,²(), 陈新兵¹, 陈沛¹

1. 陕西师范大学应用表面与胶体化学教育部重点实验室, 材料科学与工程学院, 西安 710119
2. 西安近代化学研究所, 西安 710065

收稿日期:2013-12-16 出版日期:2014-07-10 发布日期:2014-06-10
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:
陕西省自然科学基金(批准号: 2012JM2002)、陕西省科技攻关项目(批准号: 2012K08-09)、中央高校团队项目(批准号: GK261001108, GK261001009)和中央高校基本科研业务费专项资金(批准号: GK201101003, GK201302036, GK201302037)资助

Syntheses and Properties of Four-ring Liquid Crystals with Ethylene and Internal Alkyne Bridge^†

CHEN Ran¹, AN Zhongwei^1,^2,^*(), CHEN Xinbing¹, CHEN Pei¹

1. Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, School of Materials Science and Engineering, Shaanxi Normal University, Xi'an 710119, China
2. Xi'an Modern Chemistry Research Institute, Xi'an 710065, China

Received:2013-12-16 Online:2014-07-10 Published:2014-06-10
Contact: AN Zhongwei E-mail:gmecazw@163.com
Supported by:
Supported by the Natural Science Foundation of Shannxi Province, China(No.2012JM2002), the Key Science and Technology Program of Shaanxi Province, China(No.2012K08-09), the State Education for the Research Team of Central Universities, China(NosGK261001108, GK261001009), the State Education Ministry and the Fundamental Research Funds for the Central Universities, China(NosGK201101003, GK201302036, GK201302037)

摘要/Abstract

摘要：

以4-烷基反式环己基甲酸为原料, 经格氏、黄鸣龙、碘代及“一锅法”Sonogashira偶联等反应, 制备了10个含乙撑桥键二苯炔四环液晶化合物, 其结构经IR, NMR和MS确认. 利用差示扫描量热仪(DSC)、偏光显微镜(POM)和阿贝折光仪对目标化合物进行了性能测试. 结果表明, 目标化合物具有高清亮点(220~240 ℃)、宽向列相区间(59.6~99.6 ℃)和大光学各向异性(Δn>0.3), 其性能可满足液晶光学的应用要求.

关键词: 高清亮点, 炔桥键, 双折射率, 太赫兹

Abstract:

Ten four-ring liquid crystals with ethylene and internal alkyne bridge were synthesized via Grignard reaction, Huang Minglong reduction, iodination, “one-pot” Sonogashira cross-coupling reaction with trans-4-alkyl-cyclohexane-carboxylic-acid as the starting substrate. The structures of the compounds were confirmed by infrared spectrometry(IR), nuclear magnetic resonance(NMR) and mass spectra(MS). The differential scanning calorimetry(DSC), polarising optical microscopy(POM) and Abbe refractometer were used to measure their properties. The results show that the compounds possess high clearing point(220—240 ℃), broad nematic phase(59.6—99.6 ℃) and high birefringence(Δn>0.3). These properties match the requirement of liquid crystal optics.

Key words: High clearing point, Alkyne-bridge, Birefringence, Terahertz

中图分类号:

O625

TrendMD:

陈然, 安忠维, 陈新兵, 陈沛. 含乙撑桥键二苯炔四环液晶的合成及性能. 高等学校化学学报, 2014, 35(7): 1433.

CHEN Ran, AN Zhongwei, CHEN Xinbing, CHEN Pei. Syntheses and Properties of Four-ring Liquid Crystals with Ethylene and Internal Alkyne Bridge^†. Chem. J. Chinese Universities, 2014, 35(7): 1433.

图/表 8

参考文献 23

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Compd.	m. p./℃	Yield(%)	Appearance	MS, m/z(RI, %)
2-F	82.7—83.3	65	Light yellow solid	298(M⁺, 9), 283(100), 155(28), 115(11), 55(8)
3-F	87.1—88.2	70	Light yellow solid	312(M⁺, 13), 297(100), 159(15)
4-F	81.4—82.7	68	Light yellow solid	326(M⁺, 10), 311(100), 159(24), 155(43), 115(15)
5-F	79.3—79.8	72	Light yellow solid	340(M⁺, 11), 325(100), 155(40), 115(12), 55(7)
2-2	159.3—161.5	45	White solid	454(M⁺, 100), 329(66), 204(21)
3-2	150.1—152.3	43	White solid	468(M⁺, 100), 343(27), 329(32), 204(17)
4-2	133.8—136.1	45	White solid	482(M⁺, 100), 357(19), 329(29), 204(16)
5-2	127.5—130.0	36	White solid	496(M⁺, 100), 371(9), 357(9), 343(13), 329(16), 204(14)
3-3	139.1—141.7	40	White solid	482(M⁺, 65), 371(30), 343(100), 204(41)
4-3	150.8—153.4	40	White solid	496(M⁺, 100), 357(21), 343(29), 204(14)
5-3	139.5—142.1	40	White solid	510(M⁺, 100), 371(14), 343(27), 204(13)
4-4	154.6—156.8	40	White solid	510(M⁺, 100), 357(50), 204(24)
5-4	143.7—146.1	38	White solid	524(M⁺, 100), 371(23), 357(22), 204(17)
5-5	143.2—145.6	43	White solid	538(M⁺, 100), 371(29), 204(11)

Compd.	m. p./℃	Yield(%)	Appearance	MS, m/z(RI, %)
2-F	82.7—83.3	65	Light yellow solid	298(M⁺, 9), 283(100), 155(28), 115(11), 55(8)
3-F	87.1—88.2	70	Light yellow solid	312(M⁺, 13), 297(100), 159(15)
4-F	81.4—82.7	68	Light yellow solid	326(M⁺, 10), 311(100), 159(24), 155(43), 115(15)
5-F	79.3—79.8	72	Light yellow solid	340(M⁺, 11), 325(100), 155(40), 115(12), 55(7)
2-2	159.3—161.5	45	White solid	454(M⁺, 100), 329(66), 204(21)
3-2	150.1—152.3	43	White solid	468(M⁺, 100), 343(27), 329(32), 204(17)
4-2	133.8—136.1	45	White solid	482(M⁺, 100), 357(19), 329(29), 204(16)
5-2	127.5—130.0	36	White solid	496(M⁺, 100), 371(9), 357(9), 343(13), 329(16), 204(14)
3-3	139.1—141.7	40	White solid	482(M⁺, 65), 371(30), 343(100), 204(41)
4-3	150.8—153.4	40	White solid	496(M⁺, 100), 357(21), 343(29), 204(14)
5-3	139.5—142.1	40	White solid	510(M⁺, 100), 371(14), 343(27), 204(13)
4-4	154.6—156.8	40	White solid	510(M⁺, 100), 357(50), 204(24)
5-4	143.7—146.1	38	White solid	524(M⁺, 100), 371(23), 357(22), 204(17)
5-5	143.2—145.6	43	White solid	538(M⁺, 100), 371(29), 204(11)

Compd.	¹H NMR(CDCl₃, 300 MHz), δ	¹³C NMR(CDCl₃, 75 MHz), δ
2-F	0.81—0.93(m, 7H), 1.11—1.27(m, 4H), 1.43—1.50(m, 2H), 1.60(s, 6H), 1.70—1.80(m, 4H), 2.51—2.63(m, 2H), 7.08(d, J=8.0 Hz, 2H), 7.31(d, J=8.1 Hz, 2H)	11.5, 30.0, 31.6, 32.8, 32.8, 33.3, 33.3, 33.3, 37.5, 39.0, 39.6, 65.6, 82.3, 93.2, 119.9, 128.3, 131.6, 143.6
3-F	0.84—0.98(m, 7H), 1.10—1.18(m, 4H), 1.25—1.34(m, 2H), 1.42—1.48(m, 2H), 1.60(s, 6H), 1.69—1.78(m, 4H), 2.54—2.63(m, 2H), 7.08(d, J=8.0 Hz, 2H), 7.31(d, J=8.0 Hz, 2H)	14.4, 20.0, 31.6, 33.3, 33.3, 33.3, 37.5, 37.5, 39.1, 39.8, 65.6, 82.3, 93.2, 119.9, 128.3, 131.6, 143.6
4-F	0.80—0.96(m, 7H), 1.09—1.19(m, 4H), 1.23—1.32(m, 4H), 1.42—1.50(m, 2H), 1.60(s, 6H), 1.69—1.80(m, 4H), 2.53—2.62(m, 2H), 7.07(d, J=8.0 Hz, 2H), 7.31(d, J=8.1 Hz, 2H)	14.2, 23.2, 29.3, 31.6, 33.3, 33.3, 33.3, 37.2, 37.5, 37.8, 39.1, 65.6, 82.3, 93.3, 119.9, 128.3, 131.6, 143.6
5-F	0.82—0.99(m, 7H), 1.07—1.20(m, 4H), 1.21—1.32(m, 6H), 1.45—1.54(m, 2H), 1.61(s, 6H), 1.69—1.79(m, 4H), 2.53—2.65(m, 2H), 7.10(d, J=8.0 Hz, 2H), 7.32(d, J=8.0 Hz, 2H)	14.1, 22.7, 26.7, 31.6, 32.2, 33.3, 33.3, 33.3, 37.5, 37.5, 37.8, 39.0, 65.6, 82.3, 93.2, 119.9, 128.3, 131.6, 143.6
2-2	0.74—0.85(m, 14H), 1.07—1.17(m, 8H), 1.38—1.44(m, 4H), 1.65—1.73(m, 8H), 2.51—2.57(m, 4H), 7.05(d, J=7.8 Hz, 4H), 7.34(d, J=7.9 Hz, 4H)	11.5, 30.0, 32.8, 32.8, 33.3, 33.3, 33.3, 37.5, 39.1, 39.6, 99.0, 120.6, 128.4, 131.5, 143.5
3-2	0.76—0.93(m, 14H), 1.03—1.10(m, 4H), 1.12—1.21(m, 4H), 1.21—1.28(m, 2H), 1.38—1.46(m, 4H), 1.62—1.75(m, 8H), 2.49—2.60(m, 4H), 7.06(d, J=7.9 Hz, 4H), 7.34(d, J=8.0 Hz, 4H)	11.5, 14.4, 20.0, 30.0, 32.8, 32.8, 33.3, 33.3, 33.3, 37.5, 37.6, 39.1, 39.6, 39.8, 99.0, 120.6, 128.4, 131.5, 143.5
4-2	0.84—0.99(m, 14H), 1.12—1.21(m, 6H), 1.21—1.24(m, 2H), 1.25—1.31(m, 4H), 1.45—1.53(m, 4H), 1.69—1.83(m, 8H), 2.55—2.68(m, 4H), 7.13(d, J=8.0 Hz, 4H), 7.41(d, J=8.0 Hz, 4H)	11.5, 14.1, 23.0, 29.3, 30.0, 32.8, 32.8, 33.3, 33.3, 33.3, 37.2, 37.5, 37.8, 39.1, 39.6, 99.0, 120.6, 128.4, 131.5, 143.5
5-2	0.83—0.96(m, 14H), 1.12—1.22(m, 8H), 1.23—1.30(m, 6H), 1.46—1.54(m, 4H), 1.70—1.83(m, 8H), 2.57—2.72(m, 4H), 7.13(d, J=7.4 Hz, 4H), 7.42(d, J=7.5 Hz, 4H)	11.5, 14.1, 22.7, 26.7, 30.0, 32.3, 32.8, 32.8, 33.3, 33.3, 33.3, 37.5, 37.5, 37.9, 39.1, 39.6, 99.0, 120.6, 128.4, 131.5, 143.5
3-3	0.70—0.92(m, 14H), 1.01—1.16(m, 8H), 1.18—1.30(m, 4H), 1.36—1.47(m, 4H), 1.55—1.79(m, 8H), 2.44—2.65(m, 4H), 7.05(d, J=8.0 Hz, 4H), 7.34(d, J=8.0 Hz, 4H)	14.4, 20.0, 33.3, 33.3, 33.3, 37.5, 37.6, 39.1, 39.8, 99.0, 120.6, 128.4, 131.5, 143.5
4-3	0.72—0.93(m, 14H), 0.98—1.14(m, 8H), 1.16—1.29(m, 6H), 1.36—1.47(m, 4H), 1.59—1.83(m, 8H), 2.43—2.64(m, 4H), 7.06(d, J=8.0 Hz, 4H), 7.34(d, J=8.0 Hz, 4H)	14.1, 14.4, 20.0, 23.0, 29.3, 33.3, 33.3, 33.3, 37.2, 37.5, 37.9, 39.1, 39.8, 99.0, 120.6, 128.4, 131.5, 143.5
5-3	0.77—0.94(m, 14H), 1.05—1.11(m, 8H), 1.16—1.23(m, 8H), 1.38—1.44(m, 4H), 1.63—1.72(m, 8H), 2.50—2.57(m, 4H), 7.06(d, J=7.8 Hz, 4H), 7.34(d, J=7.9 Hz, 4H)	14.1, 14.4, 20.0, 22.7, 26.7, 32.3, 33.3, 33.3, 33.3, 37.5, 37.5, 37.9, 39.1, 39.8, 99.0, 120.6, 128.4, 131.5, 143.5
4-4	0.84—0.95(m, 14H), 0.98—1.13(m, 8H), 1.15—1.28(m, 8H), 1.37—1.46(m, 4H), 1.58—1.79(m, 8H), 2.36—2.69(m, 4H), 7.06(d, J=7.8 Hz, 4H), 7.34(d, J=7.8 Hz, 4H)	14.1, 23.0, 29.3, 33.3, 33.3, 33.3, 37.2, 37.5, 37.8, 39.1, 99.0, 120.6, 128.4, 131.5, 143.5
5-4	0.74—0.93(m, 14H), 1.02—1.12(m, 8H), 1.15—1.26(m, 10H), 1.35—1.47(m, 6H), 1.62—1.73(m, 8H), 2.48—2.60(m, 4H), 7.05(d, J=7.2 Hz, 4H), 7.34(d, J=7.0 Hz, 4H)	14.1, 22.7, 23.0, 26.7, 29.3, 32.3, 33.3, 33.3, 33.3, 37.2, 37.5, 37.5, 37.9, 39.1, 99.0, 120.6, 128.4, 131.5, 143.5
5-5	0.82—1.00(m, 14H), 1.10—1.19(m, 8H), 1.20—1.33(m, 12H), 1.45—1.53(m, 4H), 1.68—1.84(m, 8H), 2.52—2.71(m, 4H), 7.13(d, J=8.0 Hz, 4H), 7.42(d, J=8.0 Hz, 4H)	14.1, 22.7, 26.7, 32.2, 33.3, 33.3, 33.3, 37.5, 37.5, 37.9, 39.1, 99.0, 120.6, 128.4, 131.5, 143.5

Compd.	¹H NMR(CDCl₃, 300 MHz), δ	¹³C NMR(CDCl₃, 75 MHz), δ
2-F	0.81—0.93(m, 7H), 1.11—1.27(m, 4H), 1.43—1.50(m, 2H), 1.60(s, 6H), 1.70—1.80(m, 4H), 2.51—2.63(m, 2H), 7.08(d, J=8.0 Hz, 2H), 7.31(d, J=8.1 Hz, 2H)	11.5, 30.0, 31.6, 32.8, 32.8, 33.3, 33.3, 33.3, 37.5, 39.0, 39.6, 65.6, 82.3, 93.2, 119.9, 128.3, 131.6, 143.6
3-F	0.84—0.98(m, 7H), 1.10—1.18(m, 4H), 1.25—1.34(m, 2H), 1.42—1.48(m, 2H), 1.60(s, 6H), 1.69—1.78(m, 4H), 2.54—2.63(m, 2H), 7.08(d, J=8.0 Hz, 2H), 7.31(d, J=8.0 Hz, 2H)	14.4, 20.0, 31.6, 33.3, 33.3, 33.3, 37.5, 37.5, 39.1, 39.8, 65.6, 82.3, 93.2, 119.9, 128.3, 131.6, 143.6
4-F	0.80—0.96(m, 7H), 1.09—1.19(m, 4H), 1.23—1.32(m, 4H), 1.42—1.50(m, 2H), 1.60(s, 6H), 1.69—1.80(m, 4H), 2.53—2.62(m, 2H), 7.07(d, J=8.0 Hz, 2H), 7.31(d, J=8.1 Hz, 2H)	14.2, 23.2, 29.3, 31.6, 33.3, 33.3, 33.3, 37.2, 37.5, 37.8, 39.1, 65.6, 82.3, 93.3, 119.9, 128.3, 131.6, 143.6
5-F	0.82—0.99(m, 7H), 1.07—1.20(m, 4H), 1.21—1.32(m, 6H), 1.45—1.54(m, 2H), 1.61(s, 6H), 1.69—1.79(m, 4H), 2.53—2.65(m, 2H), 7.10(d, J=8.0 Hz, 2H), 7.32(d, J=8.0 Hz, 2H)	14.1, 22.7, 26.7, 31.6, 32.2, 33.3, 33.3, 33.3, 37.5, 37.5, 37.8, 39.0, 65.6, 82.3, 93.2, 119.9, 128.3, 131.6, 143.6
2-2	0.74—0.85(m, 14H), 1.07—1.17(m, 8H), 1.38—1.44(m, 4H), 1.65—1.73(m, 8H), 2.51—2.57(m, 4H), 7.05(d, J=7.8 Hz, 4H), 7.34(d, J=7.9 Hz, 4H)	11.5, 30.0, 32.8, 32.8, 33.3, 33.3, 33.3, 37.5, 39.1, 39.6, 99.0, 120.6, 128.4, 131.5, 143.5
3-2	0.76—0.93(m, 14H), 1.03—1.10(m, 4H), 1.12—1.21(m, 4H), 1.21—1.28(m, 2H), 1.38—1.46(m, 4H), 1.62—1.75(m, 8H), 2.49—2.60(m, 4H), 7.06(d, J=7.9 Hz, 4H), 7.34(d, J=8.0 Hz, 4H)	11.5, 14.4, 20.0, 30.0, 32.8, 32.8, 33.3, 33.3, 33.3, 37.5, 37.6, 39.1, 39.6, 39.8, 99.0, 120.6, 128.4, 131.5, 143.5
4-2	0.84—0.99(m, 14H), 1.12—1.21(m, 6H), 1.21—1.24(m, 2H), 1.25—1.31(m, 4H), 1.45—1.53(m, 4H), 1.69—1.83(m, 8H), 2.55—2.68(m, 4H), 7.13(d, J=8.0 Hz, 4H), 7.41(d, J=8.0 Hz, 4H)	11.5, 14.1, 23.0, 29.3, 30.0, 32.8, 32.8, 33.3, 33.3, 33.3, 37.2, 37.5, 37.8, 39.1, 39.6, 99.0, 120.6, 128.4, 131.5, 143.5
5-2	0.83—0.96(m, 14H), 1.12—1.22(m, 8H), 1.23—1.30(m, 6H), 1.46—1.54(m, 4H), 1.70—1.83(m, 8H), 2.57—2.72(m, 4H), 7.13(d, J=7.4 Hz, 4H), 7.42(d, J=7.5 Hz, 4H)	11.5, 14.1, 22.7, 26.7, 30.0, 32.3, 32.8, 32.8, 33.3, 33.3, 33.3, 37.5, 37.5, 37.9, 39.1, 39.6, 99.0, 120.6, 128.4, 131.5, 143.5
3-3	0.70—0.92(m, 14H), 1.01—1.16(m, 8H), 1.18—1.30(m, 4H), 1.36—1.47(m, 4H), 1.55—1.79(m, 8H), 2.44—2.65(m, 4H), 7.05(d, J=8.0 Hz, 4H), 7.34(d, J=8.0 Hz, 4H)	14.4, 20.0, 33.3, 33.3, 33.3, 37.5, 37.6, 39.1, 39.8, 99.0, 120.6, 128.4, 131.5, 143.5
4-3	0.72—0.93(m, 14H), 0.98—1.14(m, 8H), 1.16—1.29(m, 6H), 1.36—1.47(m, 4H), 1.59—1.83(m, 8H), 2.43—2.64(m, 4H), 7.06(d, J=8.0 Hz, 4H), 7.34(d, J=8.0 Hz, 4H)	14.1, 14.4, 20.0, 23.0, 29.3, 33.3, 33.3, 33.3, 37.2, 37.5, 37.9, 39.1, 39.8, 99.0, 120.6, 128.4, 131.5, 143.5
5-3	0.77—0.94(m, 14H), 1.05—1.11(m, 8H), 1.16—1.23(m, 8H), 1.38—1.44(m, 4H), 1.63—1.72(m, 8H), 2.50—2.57(m, 4H), 7.06(d, J=7.8 Hz, 4H), 7.34(d, J=7.9 Hz, 4H)	14.1, 14.4, 20.0, 22.7, 26.7, 32.3, 33.3, 33.3, 33.3, 37.5, 37.5, 37.9, 39.1, 39.8, 99.0, 120.6, 128.4, 131.5, 143.5
4-4	0.84—0.95(m, 14H), 0.98—1.13(m, 8H), 1.15—1.28(m, 8H), 1.37—1.46(m, 4H), 1.58—1.79(m, 8H), 2.36—2.69(m, 4H), 7.06(d, J=7.8 Hz, 4H), 7.34(d, J=7.8 Hz, 4H)	14.1, 23.0, 29.3, 33.3, 33.3, 33.3, 37.2, 37.5, 37.8, 39.1, 99.0, 120.6, 128.4, 131.5, 143.5
5-4	0.74—0.93(m, 14H), 1.02—1.12(m, 8H), 1.15—1.26(m, 10H), 1.35—1.47(m, 6H), 1.62—1.73(m, 8H), 2.48—2.60(m, 4H), 7.05(d, J=7.2 Hz, 4H), 7.34(d, J=7.0 Hz, 4H)	14.1, 22.7, 23.0, 26.7, 29.3, 32.3, 33.3, 33.3, 33.3, 37.2, 37.5, 37.5, 37.9, 39.1, 99.0, 120.6, 128.4, 131.5, 143.5
5-5	0.82—1.00(m, 14H), 1.10—1.19(m, 8H), 1.20—1.33(m, 12H), 1.45—1.53(m, 4H), 1.68—1.84(m, 8H), 2.52—2.71(m, 4H), 7.13(d, J=8.0 Hz, 4H), 7.42(d, J=8.0 Hz, 4H)	14.1, 22.7, 26.7, 32.2, 33.3, 33.3, 33.3, 37.5, 37.5, 37.9, 39.1, 99.0, 120.6, 128.4, 131.5, 143.5

n	m	Transition temperature /℃[Enthalpy change/(kJ·mol^-1)]
		Heating process^a				Cooling process^b
		Cr	S_A	N	I	I	N	S_A	Cr
2	2	69.9(10.7)		160.8(23.2)	220.4(4.0)	219.9(-3.8)			159.4(-20.5)
3	2	50.7(1.9)		151.4(20.1)	233.5(6.2)	232.4(-5.1)			149.0(-15.9)
4	2	73.1(2.6)		135.2(16.1)	229.0(5.6)	227.4(-5.3)			132.3(-15.6)
5	2	78.4(24.7)		128.3(10.0)	225.8(4.6)	225.2(-4.4)			127.2(-9.4)
3	3	89.4(13.0)		140.5(10.4)	240.1(1.7)	239.6(-2.1)			138.4(-10.4)
4	3	58.5(14.6)		152.2(17.1)	240.4(5.1)	239.9(-4.6)			150.9(-16.5)
5	3	88.0(24.0)		140.2(12.0)	239.3(4.4)	238.8(-4.9)			138.9(-10.1)
4	4	66.8(17.5)		155.4(6.6)	235.7(3.9)	235.3(-3.8)			154.3(-16.1)
5	4	79.5(22.1)	144.9(0.6)	146.4(7.9)	234.8(4.5)	234.3(-4.3)	146.0(-4.2)	144.3(-8.9)	40.9(-18.5)
5	5	117.6(32.6)	144.5(8.9)	156.8(5.1)	234.0(5.0)	233.8(-4.9)	156.5(-4.9)	141.8(-9.7)	95.0(-29.5)

含乙撑桥键二苯炔四环液晶的合成及性能

Syntheses and Properties of Four-ring Liquid Crystals with Ethylene and Internal Alkyne Bridge^†

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Compd.	Structure	Transition temperature/℃
Compd.	Structure	Cr	S_X1	S_X2	S_H	S_B	N	I
1		66	122	150.5		174	197.5	231
2^[20]		76	(63.5)	148		190.5	215	228
3		185						Above 300
4^[21]		202						Above 300
5		127			155	210	220	325
6^[22]		57			62	226	248	312
3-3		140.5						240.1
5-3		140.2						239.3

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含乙撑桥键二苯炔四环液晶的合成及性能

Syntheses and Properties of Four-ring Liquid Crystals with Ethylene and Internal Alkyne Bridge†

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Syntheses and Properties of Four-ring Liquid Crystals with Ethylene and Internal Alkyne Bridge^†