高等学校化学学报 ›› 2015, Vol. 36 ›› Issue (5): 899.doi: 10.7503/cjcu20141138
收稿日期:
2014-12-29
出版日期:
2015-05-10
发布日期:
2015-04-13
作者简介:
联系人简介: 郑敏燕, 女, 博士, 教授, 主要从事功能材料研究.E-mail: 基金资助:
ZHENG Minyan*(), WEI Yongsheng, GENG Wei
Received:
2014-12-29
Online:
2015-05-10
Published:
2015-04-13
Contact:
ZHENG Minyan
E-mail:zmy71@126.com
Supported by:
摘要:
以4-烷基环己基甲酸(C1~C3)、 4-烷基苯甲酸(C1~C5)和对羟基偶氮苯甲酸为主要原料, 通过室温一步酯化反应, 合成了2个系列8个不对称酯基偶氮苯甲酸类多官能团液晶化合物. 目标产物的结构、 液晶性及光敏性采用红外光谱(IR)、 核磁共振谱(NMR)、 质谱(MS)、 元素分析、 示差扫描量热分析(DSC)、 热台偏光显微镜(HS-POM)和紫外-可见光谱(UV-Vis)等表征. 利用循环伏安法(CV)测定了目标分子的前线轨道能级. 测试结果表明, 8个化合物均有液晶性, 在甲醇溶液中显现出光敏性, 在液晶态也观察到光顺反异构化. 端烷基碳原子数对化合物紫外吸收峰Ⅱ(偶氮结构π-π*带)、 HOMO能级、 LUMO能级和能隙Eg存在奇偶效应影响. 烷基为奇碳数化合物的Eg低于相邻烷基为偶碳数化合物. 这与目标分子紫外光谱变化趋势相吻合, 即Eg较小的化合物在紫外光谱中峰Ⅱ的吸收波长较长(能量较低), 反之亦然.
中图分类号:
TrendMD:
郑敏燕, 魏永生, 耿薇. 不对称三环偶氮苯甲酸液晶的合成、光敏性及电化学性质. 高等学校化学学报, 2015, 36(5): 899.
ZHENG Minyan, WEI Yongsheng, GENG Wei. Synthesis, Photosensitive and Electrochemical Properties of Asymmetric Liquid Crystals Based on Tri-ring Azo-benzoic Acid†. Chem. J. Chinese Universities, 2015, 36(5): 899.
Compd. | Appea- rance | Yield (%) | m.p./℃ | IR(KBr), | MS([M+], calcd.), m/z | Elemental analysis(%, calcd.) | ||||
---|---|---|---|---|---|---|---|---|---|---|
N | C | H | ||||||||
3a | Orange needle | 82.4 | 211.2—212.6 | 3200—2500(m, O—H), 3069, 2994, 2922, 2882(s, C—H), 1734, 1684(vs, C═O), 1602(m, N═N), 1594, 1559, 1541, 1449(m, ArH), 1428, 1276, 1222, 1201, 1178, 1074, 1010(vs, C—O—C), 879(s, trans-R—N═N—R), 807(w, 1,4-Ar), 688 [w,(CH2)n] | 366 (366.41) | 68.94 (68.84) | 6.30 (6.05) | 7.83 (7.65) | ||
Compd. | Appea- rance | Yield (%) | m.p./℃ | IR(KBr), ν/cm-1 | MS([M+], calcd.), m/z | Elemental analysis(%, calcd.) | ||||
N | C | H | ||||||||
3b | Orange needle | 80.2 | 221.7—222.8 | 3200—2500(m, O—H), 2950, 2930, 2864(s, C—H), 1755, 1697(vs, C═O), 1603(m, N═N), 1563, 1499(m, ArH), 1427, 1290, 1223, 1200, 1141, 1121, 1009(vs, C—O—C), 868(s, trans-R—N═N—R), 809(w, 1, 4-Ar), 690[w,(CH2)n] | 380 (380.44) | 69.67 (69.46) | 6.54 (6.36) | 7.49 (7.36) | ||
3c | Orange needle | 84.0 | 208.9—209.5 | 3000—2500(m, O—H), 2960, 2931(s, C—H), 1755, 1680(vs, C═O), 1603(m, N═N), 1592, 1500, 1449(m, ArH), 1428, 1290, 1224, 1201, 1142, 1122, 1101, 1076, 1010(vs, C—O—C), 869(s, trans-R—N═N—R), 808(w, 1, 4-Ar), 765 [w,(CH2)n] | 394 (394.46) | 70.22 (70.03) | 6.73 (6.64) | 7.15 (7.10) | ||
3d | Orange needle | 81.1 | 198.0—199.7 | 3000—2500(m, O—H), 3069, 2994, 2922, 2882(s, C—H), 1734, 1684(vs, C═O), 1602(m, N═N), 1594, 1559(m, ArH), 1498, 1428, 1276, 1222, 1201, 1178, 1141, 1074, 1010(vs, C—O—C), 879(s, trans-R—N═N—R), 812(w, 1, 4-Ar), 776 [w,(CH2)n] | 360 (360.11) | 70.14 (69.99) | 4.60 (4.48) | 7.93 (7.77) | ||
3e | Orange needle | 80.7 | 200.4—201.9 | 3000—2500(m, O—H), 3097, 3071, 2968, 2853(s, C—H), 1735, 1685(vs, C═O), 1602(m, N═N), 1559, 1541, 1496, 1458(m, ArH), 1266, 1223, 1195, 1177, 1142, 1068, 1009(vs, C—O—C), 882(s, trans-R—N═N—R), 811(w, 1,4-Ar), 766 [w,(CH2)n] | 374 (374.39) | 70.77 (70.58) | 4.90 (4.85) | 7.66 (7.48) | ||
3f | Orange needle | 85.2 | 199.5—200.9 | 3100—2500(m, O—H), 2958, 2929, 2871(s, C—H), 1734, 1684(vs, C═O), 1604(m, N═N), 1495, 1464(m, ArH), 1309, 1267, 1223, 1196, 1141, 1099, 1061, 1010(vs, C—O—C), 882(s, trans-R—N═N—R), 831(w, 1, 4-Ar), 776 [w,(CH2)n] | 388 (388.42) | 71.33 (71.12) | 5.30 (5.19) | 7.39 (7.21) | ||
3g | Orange needle | 88.6 | 186.3—187.8 | 3000—2500(m, O—H), 2956, 2927, 2857(s, C—H), 1734, 1681(vs, C═O), 1603(m, N═N), 1595, 1495(m, ArH), 1416, 1379, 1270, 1223, 1198, 1176, 1141, 1100, 1068, 1010(vs, C—O—C), 946, 880(s, trans-R—N═N—R), 846(w, 1, 4-Ar), 775 [w,(CH2)n] | 402 (402.44) | 71.78 (71.63) | 5.66 (5.51) | 6.75 (6.96) | ||
3h | Orange needle | 84.3 | 187.1—188.5 | 3000—2500(m, O—H), 2929, 2857(s, C—H), 1786, 1685(vs, C═O), 1602(m, N═N), 1541, 1468(m, ArH), 1417, 1358, 1287, 1255, 1220, 1142, 1101, 1041, 1008(vs, C—O—C), 943, 882(s, trans-R—N═N—R), 817(w, 1, 4-Ar), 721 [w,(CH2)n] | 416 (416.47) | 72.33 (72.10) | 5.99 (5.81) | 6.88 (6.73) |
Table 1 Appearance, yields, melting points, IR, MS data and elemental analysis of target compounds
Compd. | Appea- rance | Yield (%) | m.p./℃ | IR(KBr), | MS([M+], calcd.), m/z | Elemental analysis(%, calcd.) | ||||
---|---|---|---|---|---|---|---|---|---|---|
N | C | H | ||||||||
3a | Orange needle | 82.4 | 211.2—212.6 | 3200—2500(m, O—H), 3069, 2994, 2922, 2882(s, C—H), 1734, 1684(vs, C═O), 1602(m, N═N), 1594, 1559, 1541, 1449(m, ArH), 1428, 1276, 1222, 1201, 1178, 1074, 1010(vs, C—O—C), 879(s, trans-R—N═N—R), 807(w, 1,4-Ar), 688 [w,(CH2)n] | 366 (366.41) | 68.94 (68.84) | 6.30 (6.05) | 7.83 (7.65) | ||
Compd. | Appea- rance | Yield (%) | m.p./℃ | IR(KBr), ν/cm-1 | MS([M+], calcd.), m/z | Elemental analysis(%, calcd.) | ||||
N | C | H | ||||||||
3b | Orange needle | 80.2 | 221.7—222.8 | 3200—2500(m, O—H), 2950, 2930, 2864(s, C—H), 1755, 1697(vs, C═O), 1603(m, N═N), 1563, 1499(m, ArH), 1427, 1290, 1223, 1200, 1141, 1121, 1009(vs, C—O—C), 868(s, trans-R—N═N—R), 809(w, 1, 4-Ar), 690[w,(CH2)n] | 380 (380.44) | 69.67 (69.46) | 6.54 (6.36) | 7.49 (7.36) | ||
3c | Orange needle | 84.0 | 208.9—209.5 | 3000—2500(m, O—H), 2960, 2931(s, C—H), 1755, 1680(vs, C═O), 1603(m, N═N), 1592, 1500, 1449(m, ArH), 1428, 1290, 1224, 1201, 1142, 1122, 1101, 1076, 1010(vs, C—O—C), 869(s, trans-R—N═N—R), 808(w, 1, 4-Ar), 765 [w,(CH2)n] | 394 (394.46) | 70.22 (70.03) | 6.73 (6.64) | 7.15 (7.10) | ||
3d | Orange needle | 81.1 | 198.0—199.7 | 3000—2500(m, O—H), 3069, 2994, 2922, 2882(s, C—H), 1734, 1684(vs, C═O), 1602(m, N═N), 1594, 1559(m, ArH), 1498, 1428, 1276, 1222, 1201, 1178, 1141, 1074, 1010(vs, C—O—C), 879(s, trans-R—N═N—R), 812(w, 1, 4-Ar), 776 [w,(CH2)n] | 360 (360.11) | 70.14 (69.99) | 4.60 (4.48) | 7.93 (7.77) | ||
3e | Orange needle | 80.7 | 200.4—201.9 | 3000—2500(m, O—H), 3097, 3071, 2968, 2853(s, C—H), 1735, 1685(vs, C═O), 1602(m, N═N), 1559, 1541, 1496, 1458(m, ArH), 1266, 1223, 1195, 1177, 1142, 1068, 1009(vs, C—O—C), 882(s, trans-R—N═N—R), 811(w, 1,4-Ar), 766 [w,(CH2)n] | 374 (374.39) | 70.77 (70.58) | 4.90 (4.85) | 7.66 (7.48) | ||
3f | Orange needle | 85.2 | 199.5—200.9 | 3100—2500(m, O—H), 2958, 2929, 2871(s, C—H), 1734, 1684(vs, C═O), 1604(m, N═N), 1495, 1464(m, ArH), 1309, 1267, 1223, 1196, 1141, 1099, 1061, 1010(vs, C—O—C), 882(s, trans-R—N═N—R), 831(w, 1, 4-Ar), 776 [w,(CH2)n] | 388 (388.42) | 71.33 (71.12) | 5.30 (5.19) | 7.39 (7.21) | ||
3g | Orange needle | 88.6 | 186.3—187.8 | 3000—2500(m, O—H), 2956, 2927, 2857(s, C—H), 1734, 1681(vs, C═O), 1603(m, N═N), 1595, 1495(m, ArH), 1416, 1379, 1270, 1223, 1198, 1176, 1141, 1100, 1068, 1010(vs, C—O—C), 946, 880(s, trans-R—N═N—R), 846(w, 1, 4-Ar), 775 [w,(CH2)n] | 402 (402.44) | 71.78 (71.63) | 5.66 (5.51) | 6.75 (6.96) | ||
3h | Orange needle | 84.3 | 187.1—188.5 | 3000—2500(m, O—H), 2929, 2857(s, C—H), 1786, 1685(vs, C═O), 1602(m, N═N), 1541, 1468(m, ArH), 1417, 1358, 1287, 1255, 1220, 1142, 1101, 1041, 1008(vs, C—O—C), 943, 882(s, trans-R—N═N—R), 817(w, 1, 4-Ar), 721 [w,(CH2)n] | 416 (416.47) | 72.33 (72.10) | 5.99 (5.81) | 6.88 (6.73) |
Compd. | 1H NMR(400 MHz, CDCl3), δ |
---|---|
3a | 0.90(s, 3H, CH3), 1.40—2.97(m, 10H, 10cyclohexyl-H), 7.53, 7.97, 8.01, 8.23(d, J=8.0, 8.4, 8.8, 8.0 Hz, 2H of each, 8Ph-H), 12.96(s, 1H, COOH) |
3b | 0.89(t, 3H, J=7.6 Hz, CH3), 1.25—1.26(m, 2H, CH2), 1.25—2.18(m, 10H, 10cyclohexyl-H), 7.27, 7.64, 7.80, 8.25(d, J=8.0, 9.2, 8.8, 8.0 Hz, 2H of each, 8Ph-H), 12.81(s, 1H, COOH) |
Compd. | 1H NMR(400 MHz, CDCl3), δ |
3c | 0.88(t, 3H, J=7.2 Hz, CH3), 1.20—1.27(m, 2H, CH2), 1.24(m, 2H, CH2), 1.57—2.60(m, 10H, 10cyclohexyl-H), 7.30, 7.48, 8.01, 8.31(d, J=8.0, 8.4, 8.4, 8.0 Hz, 2H of each, 8Ph-H), 12.73(s, 1H, COOH) |
3d | 2.41(s, 3H, CH3), 7.39, 7.41, 8.01, 8.04, 8.32, 8.41(d, J=7.2, 7.2, 8.0, 8.0, 7.2, 7.2 Hz, 2H of each, 12Ph-H), 13.11(s, 1H, COOH) |
3e | 1.27(t, J=7.2 Hz, 3H, CH3), 2.74(q, J=7.2 Hz, 2H, CH2), 7.29, 7.35, 7.41, 8.03, 8.12, 8.25(d, J=8.0, 8.4, 8.4, 8.0, 8.0, 8.0 Hz, 2H of each, 12Ph-H), 12.91(s, 1H, COOH) |
3f | 0.97(t, 3H, J=7.2 Hz, CH3), 1.70(m, 2H, CH2), 2.68(t, J=7.2 Hz, 2H, CH2), 7.32, 7.34, 7.98, 8.01, 8.11, 8.35(d, J=8.0, 8.4, 8.0, 8.0, 8.0, 8.4 Hz, 2H of each, 12Ph-H), 12.86(s, 1H, COOH) |
3g | 0.90(t, 3H, J=7.2 Hz, CH3), 1.29—1.37(m, 2H, CH2), 1.54—1.65(m, 2H, CH2), 2.66(t, J=7.2 Hz, 2H, CH2), 7.29, 7.36, 7.97, 8.02, 8.09, 8.22(d, J=8.4, 8.8, 8.4, 8.8, 8.0, 8.4 Hz, 2H of each, 12Ph-H), 13.01(s, 1H, COOH) |
3h | 0.90(t, 3H, J=6.8 Hz, CH3), 1.25—1.44(m, 6H, CH2CH2CH2), 1.64(t, 2H, J=7.2 Hz, CH2), 7.28, 7.32, 8.03, 8.06, 8.22, 8.28(d, J=8.4, 8.4, 8.0, 8.4, 8.0, 8.4 Hz, 2H of each, 12Ph-H), 13.02(s, 1H, COOH) |
Table 2 1H NMR data for target compounds
Compd. | 1H NMR(400 MHz, CDCl3), δ |
---|---|
3a | 0.90(s, 3H, CH3), 1.40—2.97(m, 10H, 10cyclohexyl-H), 7.53, 7.97, 8.01, 8.23(d, J=8.0, 8.4, 8.8, 8.0 Hz, 2H of each, 8Ph-H), 12.96(s, 1H, COOH) |
3b | 0.89(t, 3H, J=7.6 Hz, CH3), 1.25—1.26(m, 2H, CH2), 1.25—2.18(m, 10H, 10cyclohexyl-H), 7.27, 7.64, 7.80, 8.25(d, J=8.0, 9.2, 8.8, 8.0 Hz, 2H of each, 8Ph-H), 12.81(s, 1H, COOH) |
Compd. | 1H NMR(400 MHz, CDCl3), δ |
3c | 0.88(t, 3H, J=7.2 Hz, CH3), 1.20—1.27(m, 2H, CH2), 1.24(m, 2H, CH2), 1.57—2.60(m, 10H, 10cyclohexyl-H), 7.30, 7.48, 8.01, 8.31(d, J=8.0, 8.4, 8.4, 8.0 Hz, 2H of each, 8Ph-H), 12.73(s, 1H, COOH) |
3d | 2.41(s, 3H, CH3), 7.39, 7.41, 8.01, 8.04, 8.32, 8.41(d, J=7.2, 7.2, 8.0, 8.0, 7.2, 7.2 Hz, 2H of each, 12Ph-H), 13.11(s, 1H, COOH) |
3e | 1.27(t, J=7.2 Hz, 3H, CH3), 2.74(q, J=7.2 Hz, 2H, CH2), 7.29, 7.35, 7.41, 8.03, 8.12, 8.25(d, J=8.0, 8.4, 8.4, 8.0, 8.0, 8.0 Hz, 2H of each, 12Ph-H), 12.91(s, 1H, COOH) |
3f | 0.97(t, 3H, J=7.2 Hz, CH3), 1.70(m, 2H, CH2), 2.68(t, J=7.2 Hz, 2H, CH2), 7.32, 7.34, 7.98, 8.01, 8.11, 8.35(d, J=8.0, 8.4, 8.0, 8.0, 8.0, 8.4 Hz, 2H of each, 12Ph-H), 12.86(s, 1H, COOH) |
3g | 0.90(t, 3H, J=7.2 Hz, CH3), 1.29—1.37(m, 2H, CH2), 1.54—1.65(m, 2H, CH2), 2.66(t, J=7.2 Hz, 2H, CH2), 7.29, 7.36, 7.97, 8.02, 8.09, 8.22(d, J=8.4, 8.8, 8.4, 8.8, 8.0, 8.4 Hz, 2H of each, 12Ph-H), 13.01(s, 1H, COOH) |
3h | 0.90(t, 3H, J=6.8 Hz, CH3), 1.25—1.44(m, 6H, CH2CH2CH2), 1.64(t, 2H, J=7.2 Hz, CH2), 7.28, 7.32, 8.03, 8.06, 8.22, 8.28(d, J=8.4, 8.4, 8.0, 8.4, 8.0, 8.4 Hz, 2H of each, 12Ph-H), 13.02(s, 1H, COOH) |
Entry | Compd. | λmax/nm | f(cis)t(%) | Time of isomerization/min | ||||
---|---|---|---|---|---|---|---|---|
Trans isomer | Cis isomer | |||||||
Ⅰ | Ⅱ | Ⅰ | Ⅱ | Solution | Mesophase | |||
1 | 3a | 233 | 347 | 235 | 354 | 11 | 40 | 50 |
3b | 223 | 330 | 223 | 327 | 55 | 40 | 70 | |
3c | 230 | 334 | 229 | 335 | 38 | 50 | 80 | |
2 | 3d | 238 | 340 | 238 | 334 | 37 | 70 | 90 |
3e | 239 | 337 | 240 | 334 | 50 | 70 | 90 | |
3f | 239 | 339 | 239 | 338 | 37 | 60 | 80 | |
3g | 238 | 336 | 239 | 333 | 29 | 60 | 70 | |
3h | 239 | 338 | 238 | 333 | 16 | 50 | 70 |
Table 3 UV spectrum of target compounds and the maximum time of isomerization
Entry | Compd. | λmax/nm | f(cis)t(%) | Time of isomerization/min | ||||
---|---|---|---|---|---|---|---|---|
Trans isomer | Cis isomer | |||||||
Ⅰ | Ⅱ | Ⅰ | Ⅱ | Solution | Mesophase | |||
1 | 3a | 233 | 347 | 235 | 354 | 11 | 40 | 50 |
3b | 223 | 330 | 223 | 327 | 55 | 40 | 70 | |
3c | 230 | 334 | 229 | 335 | 38 | 50 | 80 | |
2 | 3d | 238 | 340 | 238 | 334 | 37 | 70 | 90 |
3e | 239 | 337 | 240 | 334 | 50 | 70 | 90 | |
3f | 239 | 339 | 239 | 338 | 37 | 60 | 80 | |
3g | 238 | 336 | 239 | 333 | 29 | 60 | 70 | |
3h | 239 | 338 | 238 | 333 | 16 | 50 | 70 |
Fig.1 UV-Vis absorption spectra of compound 3b in methanol during trans-to-cis isomerization Fig.1(B) illustrates the small increase of absorption in 430 nm. Time/min: a. 0; b. 10; c. 20; d. 30; e. 40.
Entry | Compd. | Eox/eV | Φp/eV | Ered/eV | Φn/eV | EHOMO/eV | ELUMO/eV | Eg/eV | ||
---|---|---|---|---|---|---|---|---|---|---|
Ⅰ | Ⅱ | Ⅰ | Ⅱ | |||||||
1 | 3a | 0.69 | 0.66 | 0.66 | -0.49 | -0.62 | -0.49 | -5.06 | -3.91 | 1.15 |
3b | 0.76 | 0.76 | -0.42 | -0.60 | -0.42 | -5.16 | -3.98 | 1.18 | ||
3c | 0.76 | 0.63 | 0.63 | -0.53 | -0.64 | -0.53 | -5.03 | -3.87 | 1.16 | |
2 | 3d | 0.82 | 0.65 | 0.65 | -0.47 | -0.56 | -0.47 | -5.05 | -3.93 | 1.12 |
3e | 0.88 | 0.88 | -0.51 | -0.65 | -0.51 | -5.28 | -3.89 | 1.39 | ||
3f | 0.82 | 0.82 | -0.45 | -0.54 | -0.45 | -5.22 | -3.95 | 1.27 | ||
3g | 0.83 | 0.83 | -0.54 | -0.64 | -0.54 | -5.23 | -3.86 | 1.37 | ||
3h | 0.81 | 0.58 | 0.58 | -0.50 | -0.62 | -0.50 | -4.98 | -3.90 | 1.08 |
Table 4 Redox potentials, EHOMO, ELUMO and energy gaps of target compounds
Entry | Compd. | Eox/eV | Φp/eV | Ered/eV | Φn/eV | EHOMO/eV | ELUMO/eV | Eg/eV | ||
---|---|---|---|---|---|---|---|---|---|---|
Ⅰ | Ⅱ | Ⅰ | Ⅱ | |||||||
1 | 3a | 0.69 | 0.66 | 0.66 | -0.49 | -0.62 | -0.49 | -5.06 | -3.91 | 1.15 |
3b | 0.76 | 0.76 | -0.42 | -0.60 | -0.42 | -5.16 | -3.98 | 1.18 | ||
3c | 0.76 | 0.63 | 0.63 | -0.53 | -0.64 | -0.53 | -5.03 | -3.87 | 1.16 | |
2 | 3d | 0.82 | 0.65 | 0.65 | -0.47 | -0.56 | -0.47 | -5.05 | -3.93 | 1.12 |
3e | 0.88 | 0.88 | -0.51 | -0.65 | -0.51 | -5.28 | -3.89 | 1.39 | ||
3f | 0.82 | 0.82 | -0.45 | -0.54 | -0.45 | -5.22 | -3.95 | 1.27 | ||
3g | 0.83 | 0.83 | -0.54 | -0.64 | -0.54 | -5.23 | -3.86 | 1.37 | ||
3h | 0.81 | 0.58 | 0.58 | -0.50 | -0.62 | -0.50 | -4.98 | -3.90 | 1.08 |
Entry | Compd. | L/Wa | m.p./℃ | ΔH of m.p./(J·g-1) | d.p.b/℃ |
---|---|---|---|---|---|
1 | 3a | 4.362 | 211.2 | 28.72 | 218—369 |
3b | 4.638 | 221.0 | 26.54 | 232—419 | |
3c | 4.967 | 208.2 | 23.17 | 226—425 | |
2 | 3d | 4.110 | 198.7 | 25.62 | 257—413 |
3e | 4.447 | 200.3 | 26.76 | 246—388 | |
3f | 4.497 | 199.1 | 21.82 | 230—429 | |
3g | 4.549 | 186.8 | 40.39 | 240—393 | |
3h | 4.722 | 187.9 | 27.67 | 230—349 |
Table 5 DSC measurement results of target compounds
Entry | Compd. | L/Wa | m.p./℃ | ΔH of m.p./(J·g-1) | d.p.b/℃ |
---|---|---|---|---|---|
1 | 3a | 4.362 | 211.2 | 28.72 | 218—369 |
3b | 4.638 | 221.0 | 26.54 | 232—419 | |
3c | 4.967 | 208.2 | 23.17 | 226—425 | |
2 | 3d | 4.110 | 198.7 | 25.62 | 257—413 |
3e | 4.447 | 200.3 | 26.76 | 246—388 | |
3f | 4.497 | 199.1 | 21.82 | 230—429 | |
3g | 4.549 | 186.8 | 40.39 | 240—393 | |
3h | 4.722 | 187.9 | 27.67 | 230—349 |
Fig.2 POM images of compounds 3a—3h during heating process(A)—(H) Schlieren textures of 3a, 3b, 3c, 3d, 3e, 3f, 3g and 3h taken at 214, 227, 228, 221, 220, 210, 220 and 220 ℃, respectively.
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