光响应偶氮苯类小分子凝胶因子的合成及性能

doi:10.7503/cjcu20140195

摘要/Abstract

摘要：

合成了3个系列各6类的偶氮苯衍生物1a~6a, 1b~6b和1c~6c. 凝胶性能测试结果表明, 这些化合物均能在多种极性或非极性有机溶剂中形成凝胶. 运用扫描电子显微镜和核磁共振波谱仪对代表性化合物4b形成的凝胶结构和成胶驱动力进行了分析. 化合物4a~4c形成的凝胶在紫外光和可见光照射下, 能够发生凝胶-溶胶的相互转化. 计算了溶剂和凝胶因子的梯氏参数, 利用梯氏三角图分析了凝胶测试结果, 发现凝胶因子在溶剂中的4种行为(溶液、半凝胶、凝胶和沉淀)分别分布在三角图的不同区域; 在凝胶区域, 溶剂与凝胶因子之间的距离反映了凝胶的热稳定性, 距离越远表示凝胶的热稳定性越好.

关键词: 偶氮苯, 凝胶, 光响应, 梯氏参数

Abstract:

Eighteen azobenzene derivatives, 1a—6a, 1b—6b and 1c—6c, were synthesized and their gelation behaviors were tested. The synthesized azobenzenes readily formed stable gels in many polar or apolar organic solvents. As the representative, the structures of gels from compound 4b and the driving force of the gel formation were investigated by SEM and ¹H NMR. The photoresponse of the gels from compounds 4a—4c was studied and they all showed gel-sol transition under UV light irradiation while sol-gel transition in visible light radiation. Teas parameters of the solvents and gelators were systematically calculated and presented in the Teas plots. The results show that the four gelation behaviors(solution, partial gelation, gelation and precipitation) are located in different regions respectively. In the region of gelation, the distance between the solvent and the gelator reflects the thermal stability of the gel, the farther the distance is, the better the thermal stability of the gel will be.

Key words: Azobenzene, Gelation, Photoresponse, Teas parameter

中图分类号:

O648.17

TrendMD:

樊冬丽, 翟岩, 张妍, 涂伟, 黄耀东. 光响应偶氮苯类小分子凝胶因子的合成及性能. 高等学校化学学报, 2014, 35(11): 2447.

FAN Dongli, ZHAI Yan, ZHANG Yan, TU Wei, HUANG Yaodong. Synthesis and Properties of Photoresponsive Organogels Based on Azobenzene Derivatives. Chem. J. Chinese Universities, 2014, 35(11): 2447.

图/表 8

参考文献 23

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Compd.	¹H NMR(300 MHz, CDCl₃), δ	m.p./ ℃	Yield (%)	GC-MS [M+H]⁺, m/z
1a	7.90(d, J=9.1 Hz, 2H, HAr), 7.83(d, J=8.4 Hz, 2H, H—Ar), 7.61(d, J=8.7 Hz, 2H, H—Ar), 6.97(d, J=9.1 Hz, 2H, H—Ar), 4.06(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.89(m,8H,CH₂), 0.9[t, J=6.6 Hz, 3H,—O(CH₂)₅CH₃]	113—115	92	409.1
1b	7.91(d, J=9.1 Hz, 2H, H—Ar), 7.84(d, J=8.7 Hz, 2H, H—Ar), 7.62(d, J=8.7 Hz, 2H, H—Ar), 6.98(d, J=9.1 Hz, 2H, H—Ar), 4.02(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.89(m, 20H, CH₂), 0.9[t, J=6.6 Hz, 3H,—O(CH₂)₁₁CH₃]	107—109	95	493.2
1c	7.89(d, J=9.1 Hz, 2H, H—Ar), 7.82(d, J=8.4 Hz, 2H, H—Ar), 7.61(d, J=8.7 Hz, 2H, H—Ar), 6.99(d, J=9.1 Hz, 2H, H—Ar), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.89(m, 28H, CH₂), 0.9[t, J=6.6 Hz, 3H,—O(CH₂)₁₅CH₃]	109—110	94	549.3
2a	7.92(d, J=9.1 Hz, 2H, H—Ar), 7.84(d, J=8.4 Hz, 2H, H—Ar), 7.63(d, J=8.7 Hz, 2H, H—Ar), 6.94(d, J=9.1 Hz, 2H, H—Ar), 3.99(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.89(m, 8H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₅CH₃], 0.083(s, 9H, CH₃)	100—102	81	379.1
2b	7.91(d, J=9.1Hz, 2H, H—Ar), 7.82(d, J=8.4 Hz, 2H, H—Ar), 7.61(d, J=8.7 Hz, 2H, H—Ar), 6.95(d, J=9.1 Hz, 2H, H—Ar), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.89(m, 20H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₁CH₃], 0.084(s, 9H, CH₃)	105—106	80	463.2
2c	7.89(d, J=9.1 Hz, 2H, H—Ar), 7.81(d, J=8.4 Hz, 2H, H—Ar), 7.61(d, J=8.7 Hz, 2H, H—Ar), 6.94(d, J=9.1 Hz, 2H, H—Ar), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.89(m, 28H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₅CH₃], 0.083(s, 9H, CH₃)	86—88	78	519.3
Compd.	¹H NMR(300 MHz,CDCl₃), δ	m.p./ ℃	Yield (%)	GC-MS [M+H]⁺, m/z
3a	7.89(d, J=9.1 Hz, 2H, H—Ar), 7.82(d, J=8.4 Hz, 2H, H—Ar), 7.61(d, J=8.7 Hz, 2H, H—Ar), 6.94(d, J=9.1 Hz, 2H, H—Ar), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 3.1(s, 1H), 1.32—1.89(m, 8H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₅CH₃]	89—91	72	307.1
3b	7.89(d, J=9.1 Hz, 2H, H—Ar), 7.82(d, J=8.4 Hz, 2H, H—Ar), 7.61(d, J=8.7 Hz, 2H, H—Ar), 6.94(d, J=9.1 Hz, 2H, H—Ar), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 3.1(s, 1H), 1.32—1.89(m, 20H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₁CH₃]	90—92	75	391.2
3c	7.89(d, J=9.1 Hz, 2H, H—Ar), 7.82(d, J=8.4 Hz, 2H, H—Ar), 7.61(d, J=8.7 Hz, 2H, H—Ar), 6.94(d, J=9.1 Hz, 2H, H—Ar), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 3.1(s, 1H), 1.32—1.89(m, 28H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₅CH₃]	99—101	74	447.3
4a	7.91(d, J=9.0 Hz, 2H, H—Ar), 7.87(d, J=8.7 Hz, 2H, H—Ar), 7.52(d, J=8.2 Hz, 2H, H—Ar), 6.99(d, J=9.0 Hz, 2H, H—Ar), 4.77(s, 2H, —CH₂OH), 4.04(t, J=6.6 Hz, 2H, —OCH₂), 1.75—1.86(m, 2H,CH₂), 1.68(s, 1H, OH), 1.32—1.51(m, 6H, CH₂), 0.9(t, J=6.6 Hz, 3H, —O(CH₂)₁₅CH₃)	118—120	94	313.2
4b	7.91(d, J=9.1 Hz, 2H, H—Ar), 7.87(d, J=8.4 Hz, 2H, H—Ar), 7.55(d, J=8.4 Hz, 2H, H—Ar), 6.99(d, J=8.9 Hz, 2H, H—Ar), 4.77(s, 2H, —CH₂OH), 4.04(t, J=6.6 Hz, 2H, —OCH₂), 1.75—1.86(m, 2H, CH₂), 1.68(s, 1H, OH), 1.32—1.51(m, 18H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₅CH₃]	104—106	95	397.3
4c	7.91(d, J=9.1 Hz, 2H, H—Ar), 7.87(d, J=8.4 Hz, 2H, H—Ar), 7.55(d, J=8.4 Hz, 2H, H—Ar), 6.99(d, J=8.9 Hz, 2H, H—Ar), 4.77(s, 2H, —CH₂OH), 4.04(t, J=6.6 Hz, 2H, —OCH₂), 1.75—1.86(m, 2H, CH₂), 1.68(s, 1H, OH), 1.32—1.51(m, 26H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₅CH₃]	118—120	95	453.4
5a	7.91(d, J=9.1 Hz, 2H, H—Ar), 7.87(d, J=8.4 Hz, 2H, H—Ar), 7.53(d, J=8.7 Hz, 2H, H—Ar), 6.97(d, J=9.1 Hz, 2H, H—Ar), 4.64(s, 2H, —CH₂Cl), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.87(m, 8H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₅CH₃]	72—74	83	331.1
5b	7.91(d, J=9.1 Hz, 2H, H—Ar), 7.87(d, J=8.4 Hz, 2H, H—Ar), 7.53(d, J=8.7 Hz, 2H, H—Ar), 6.97(d, J=9.1 Hz, 2H, H—Ar), 4.64(s, 2H, —CH₂Cl), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.87(m, 20H, CH₂), 0.9[t, J=6.6 Hz, 3H,—O(CH₂)₁₁CH₃]	88—89	85	415.2
5c	7.91(d, J=9.1 Hz, 2H, H—Ar), 7.87(d, J=8.4 Hz, 2H, H—Ar), 7.53(d, J=8.7 Hz, 2H, H—Ar), 6.97(d, J=9.1 Hz, 2H, H—Ar), 4.64(s, 2H, —CH₂Cl), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.87(m, 28H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₅CH₃]	93—95	84	471.2
6a	7.82(d, J=9.1 Hz, 2H, H—Ar), 7.79(d, J=8.4 Hz, 2H, H—Ar), 7.53(d, J=8.7 Hz, 2H, H—Ar), 6.97(d, J=9.1 Hz, 2H, H—Ar), 4.40(s,2H, —CH₂N₃), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.87(m, 8H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₅CH₃]	61—63	82	331.9
6b	7.81(d, J=9.1 Hz, 2H, H—Ar), 7.79(d, J=8.4 Hz, 2H, H—Ar), 7.53(d, J=8.7 Hz, 2H, H—Ar), 6.97(d, J=9.1 Hz, 2H, H—Ar), 4.40(s, 2H, —CH₂N₃), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.87(m, 20H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₁CH₃]	78—80	80	422.6
6c	7.81(d, J=9.1 Hz, 2H, H—Ar), 7.79(d, J=8.4 Hz, 2H, H—Ar), 7.53(d, J=8.7 Hz, 2H, H—Ar), 6.97(d, J=9.1 Hz, 2H, H—Ar), 4.40(s, 2H, —CH₂N₃), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.87(m, 28H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₅CH₃]	89—91	79	472.1

Compd.	¹H NMR(300 MHz, CDCl₃), δ	m.p./ ℃	Yield (%)	GC-MS [M+H]⁺, m/z
1a	7.90(d, J=9.1 Hz, 2H, HAr), 7.83(d, J=8.4 Hz, 2H, H—Ar), 7.61(d, J=8.7 Hz, 2H, H—Ar), 6.97(d, J=9.1 Hz, 2H, H—Ar), 4.06(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.89(m,8H,CH₂), 0.9[t, J=6.6 Hz, 3H,—O(CH₂)₅CH₃]	113—115	92	409.1
1b	7.91(d, J=9.1 Hz, 2H, H—Ar), 7.84(d, J=8.7 Hz, 2H, H—Ar), 7.62(d, J=8.7 Hz, 2H, H—Ar), 6.98(d, J=9.1 Hz, 2H, H—Ar), 4.02(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.89(m, 20H, CH₂), 0.9[t, J=6.6 Hz, 3H,—O(CH₂)₁₁CH₃]	107—109	95	493.2
1c	7.89(d, J=9.1 Hz, 2H, H—Ar), 7.82(d, J=8.4 Hz, 2H, H—Ar), 7.61(d, J=8.7 Hz, 2H, H—Ar), 6.99(d, J=9.1 Hz, 2H, H—Ar), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.89(m, 28H, CH₂), 0.9[t, J=6.6 Hz, 3H,—O(CH₂)₁₅CH₃]	109—110	94	549.3
2a	7.92(d, J=9.1 Hz, 2H, H—Ar), 7.84(d, J=8.4 Hz, 2H, H—Ar), 7.63(d, J=8.7 Hz, 2H, H—Ar), 6.94(d, J=9.1 Hz, 2H, H—Ar), 3.99(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.89(m, 8H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₅CH₃], 0.083(s, 9H, CH₃)	100—102	81	379.1
2b	7.91(d, J=9.1Hz, 2H, H—Ar), 7.82(d, J=8.4 Hz, 2H, H—Ar), 7.61(d, J=8.7 Hz, 2H, H—Ar), 6.95(d, J=9.1 Hz, 2H, H—Ar), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.89(m, 20H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₁CH₃], 0.084(s, 9H, CH₃)	105—106	80	463.2
2c	7.89(d, J=9.1 Hz, 2H, H—Ar), 7.81(d, J=8.4 Hz, 2H, H—Ar), 7.61(d, J=8.7 Hz, 2H, H—Ar), 6.94(d, J=9.1 Hz, 2H, H—Ar), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.89(m, 28H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₅CH₃], 0.083(s, 9H, CH₃)	86—88	78	519.3
Compd.	¹H NMR(300 MHz,CDCl₃), δ	m.p./ ℃	Yield (%)	GC-MS [M+H]⁺, m/z
3a	7.89(d, J=9.1 Hz, 2H, H—Ar), 7.82(d, J=8.4 Hz, 2H, H—Ar), 7.61(d, J=8.7 Hz, 2H, H—Ar), 6.94(d, J=9.1 Hz, 2H, H—Ar), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 3.1(s, 1H), 1.32—1.89(m, 8H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₅CH₃]	89—91	72	307.1
3b	7.89(d, J=9.1 Hz, 2H, H—Ar), 7.82(d, J=8.4 Hz, 2H, H—Ar), 7.61(d, J=8.7 Hz, 2H, H—Ar), 6.94(d, J=9.1 Hz, 2H, H—Ar), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 3.1(s, 1H), 1.32—1.89(m, 20H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₁CH₃]	90—92	75	391.2
3c	7.89(d, J=9.1 Hz, 2H, H—Ar), 7.82(d, J=8.4 Hz, 2H, H—Ar), 7.61(d, J=8.7 Hz, 2H, H—Ar), 6.94(d, J=9.1 Hz, 2H, H—Ar), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 3.1(s, 1H), 1.32—1.89(m, 28H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₅CH₃]	99—101	74	447.3
4a	7.91(d, J=9.0 Hz, 2H, H—Ar), 7.87(d, J=8.7 Hz, 2H, H—Ar), 7.52(d, J=8.2 Hz, 2H, H—Ar), 6.99(d, J=9.0 Hz, 2H, H—Ar), 4.77(s, 2H, —CH₂OH), 4.04(t, J=6.6 Hz, 2H, —OCH₂), 1.75—1.86(m, 2H,CH₂), 1.68(s, 1H, OH), 1.32—1.51(m, 6H, CH₂), 0.9(t, J=6.6 Hz, 3H, —O(CH₂)₁₅CH₃)	118—120	94	313.2
4b	7.91(d, J=9.1 Hz, 2H, H—Ar), 7.87(d, J=8.4 Hz, 2H, H—Ar), 7.55(d, J=8.4 Hz, 2H, H—Ar), 6.99(d, J=8.9 Hz, 2H, H—Ar), 4.77(s, 2H, —CH₂OH), 4.04(t, J=6.6 Hz, 2H, —OCH₂), 1.75—1.86(m, 2H, CH₂), 1.68(s, 1H, OH), 1.32—1.51(m, 18H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₅CH₃]	104—106	95	397.3
4c	7.91(d, J=9.1 Hz, 2H, H—Ar), 7.87(d, J=8.4 Hz, 2H, H—Ar), 7.55(d, J=8.4 Hz, 2H, H—Ar), 6.99(d, J=8.9 Hz, 2H, H—Ar), 4.77(s, 2H, —CH₂OH), 4.04(t, J=6.6 Hz, 2H, —OCH₂), 1.75—1.86(m, 2H, CH₂), 1.68(s, 1H, OH), 1.32—1.51(m, 26H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₅CH₃]	118—120	95	453.4
5a	7.91(d, J=9.1 Hz, 2H, H—Ar), 7.87(d, J=8.4 Hz, 2H, H—Ar), 7.53(d, J=8.7 Hz, 2H, H—Ar), 6.97(d, J=9.1 Hz, 2H, H—Ar), 4.64(s, 2H, —CH₂Cl), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.87(m, 8H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₅CH₃]	72—74	83	331.1
5b	7.91(d, J=9.1 Hz, 2H, H—Ar), 7.87(d, J=8.4 Hz, 2H, H—Ar), 7.53(d, J=8.7 Hz, 2H, H—Ar), 6.97(d, J=9.1 Hz, 2H, H—Ar), 4.64(s, 2H, —CH₂Cl), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.87(m, 20H, CH₂), 0.9[t, J=6.6 Hz, 3H,—O(CH₂)₁₁CH₃]	88—89	85	415.2
5c	7.91(d, J=9.1 Hz, 2H, H—Ar), 7.87(d, J=8.4 Hz, 2H, H—Ar), 7.53(d, J=8.7 Hz, 2H, H—Ar), 6.97(d, J=9.1 Hz, 2H, H—Ar), 4.64(s, 2H, —CH₂Cl), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.87(m, 28H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₅CH₃]	93—95	84	471.2
6a	7.82(d, J=9.1 Hz, 2H, H—Ar), 7.79(d, J=8.4 Hz, 2H, H—Ar), 7.53(d, J=8.7 Hz, 2H, H—Ar), 6.97(d, J=9.1 Hz, 2H, H—Ar), 4.40(s,2H, —CH₂N₃), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.87(m, 8H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₅CH₃]	61—63	82	331.9
6b	7.81(d, J=9.1 Hz, 2H, H—Ar), 7.79(d, J=8.4 Hz, 2H, H—Ar), 7.53(d, J=8.7 Hz, 2H, H—Ar), 6.97(d, J=9.1 Hz, 2H, H—Ar), 4.40(s, 2H, —CH₂N₃), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.87(m, 20H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₁CH₃]	78—80	80	422.6
6c	7.81(d, J=9.1 Hz, 2H, H—Ar), 7.79(d, J=8.4 Hz, 2H, H—Ar), 7.53(d, J=8.7 Hz, 2H, H—Ar), 6.97(d, J=9.1 Hz, 2H, H—Ar), 4.40(s, 2H, —CH₂N₃), 4.01(t, J=6.6 Hz, 2H, —OCH₂), 1.32—1.87(m, 28H, CH₂), 0.9[t, J=6.6 Hz, 3H, —O(CH₂)₁₅CH₃]	89—91	79	472.1

Solvent	Minimum gel concentration/(mg·mL^-1)
Solvent	1a	1b	1c	2a	2b	2c	3a	3b	3c	4a	4b	4c	5a	5b	5c	6a	6b	6c
PE	100	P	P	100	100	55	100	P	P	Ins	Ins	44	PG	20	P	PG	67	P
Cyclohexane	PG	P	P	PG	PG	P	PG	P	P	27	P	53	PG	40	56	PG	PG	P
Hexane	100	P	P	PG	80	P	67	80	P	Ins	P	40	PG	23	P	PG	50	P
DCM	PG	40	50	PG	100	S	PG	40	100	57	20	10	PG	100	S	PG	PG	S
DCE	PG	33	20	P	P	P	P	P	P	26	20	26	P	P	P	P	P	P
Chloroform	PG	100	PG	S	PG	S	S	PG	S	80	80	PG	S	PG	S	S	PG	S
CTC	20	P	PG	S	PG	PG	PG	P	P	36	P	PG	S	PG	P	S	PG	PG
Ethyl acetate	PG	80	PG	PG	100	PG	PG	80	P	80	57	P	S	50	PG	S	PG	55
THF	S	PG	S	S	PG	S	S	PG	P	S	20	PG	S	PG	S	S	PG	PG
Methanol	PG	68	PG	83	P	PG	83	P	35	33	50	53	56	100	P	PG	80	37
Ethanol	67	71	35	83	48	35	100	40	PG	40	20	53	100	49	P	PG	36	P
Acetonitrile	67	68	18	43	32	55	77	28	15	57	19	26	PG	24	37	67	22	27
Isopropanol	50	100	35	59	100	PG	59	PG	P	33	100	PG	100	60	P	67	40	P
Butanol	56	50	20	83	75	30	56	60	24	40	30	18	PG	40	24	62	40	21
Acetone	PG	100	27	PG	PG	50	PG	PG	P	PG	100	29	S	PG	56	S	80	37
Ether	PG	100	Ins	PG	PG	Ins	PG	P	Ins	PG	100	Ins	PG	80	Ins	PG	80	Ins
Benzene	PG	S	55	S	PG	S	S	PG	P	80	P	53	S	S	P	S	PG	P
Toluene	S	PG	P	S	PG	S	S	PG	S	PG	PG	P	S	P	PG	S	PG	S
Dioxane	PG	S	55	S	PG	PG	S	PG	P	50	S	PG	S	80	PG	S	PG	55
Triethylamine	PG	PG	PG	PG	PG	P	PG	PG	P	S	P	PG	PG	PG	30	PG	PG	P
Pyridine	S	PG	37	S	PG	S	S	PG	P	S	S	PG	S	S	37	S	80	S

Solvent	Minimum gel concentration/(mg·mL^-1)
Solvent	1a	1b	1c	2a	2b	2c	3a	3b	3c	4a	4b	4c	5a	5b	5c	6a	6b	6c
PE	100	P	P	100	100	55	100	P	P	Ins	Ins	44	PG	20	P	PG	67	P
Cyclohexane	PG	P	P	PG	PG	P	PG	P	P	27	P	53	PG	40	56	PG	PG	P
Hexane	100	P	P	PG	80	P	67	80	P	Ins	P	40	PG	23	P	PG	50	P
DCM	PG	40	50	PG	100	S	PG	40	100	57	20	10	PG	100	S	PG	PG	S
DCE	PG	33	20	P	P	P	P	P	P	26	20	26	P	P	P	P	P	P
Chloroform	PG	100	PG	S	PG	S	S	PG	S	80	80	PG	S	PG	S	S	PG	S
CTC	20	P	PG	S	PG	PG	PG	P	P	36	P	PG	S	PG	P	S	PG	PG
Ethyl acetate	PG	80	PG	PG	100	PG	PG	80	P	80	57	P	S	50	PG	S	PG	55
THF	S	PG	S	S	PG	S	S	PG	P	S	20	PG	S	PG	S	S	PG	PG
Methanol	PG	68	PG	83	P	PG	83	P	35	33	50	53	56	100	P	PG	80	37
Ethanol	67	71	35	83	48	35	100	40	PG	40	20	53	100	49	P	PG	36	P
Acetonitrile	67	68	18	43	32	55	77	28	15	57	19	26	PG	24	37	67	22	27
Isopropanol	50	100	35	59	100	PG	59	PG	P	33	100	PG	100	60	P	67	40	P
Butanol	56	50	20	83	75	30	56	60	24	40	30	18	PG	40	24	62	40	21
Acetone	PG	100	27	PG	PG	50	PG	PG	P	PG	100	29	S	PG	56	S	80	37
Ether	PG	100	Ins	PG	PG	Ins	PG	P	Ins	PG	100	Ins	PG	80	Ins	PG	80	Ins
Benzene	PG	S	55	S	PG	S	S	PG	P	80	P	53	S	S	P	S	PG	P
Toluene	S	PG	P	S	PG	S	S	PG	S	PG	PG	P	S	P	PG	S	PG	S
Dioxane	PG	S	55	S	PG	PG	S	PG	P	50	S	PG	S	80	PG	S	PG	55
Triethylamine	PG	PG	PG	PG	PG	P	PG	PG	P	S	P	PG	PG	PG	30	PG	PG	P
Pyridine	S	PG	37	S	PG	S	S	PG	P	S	S	PG	S	S	37	S	80	S

Solvent volume ratio	9:1	8:2	7:3	6:4	5:5	4:6	3:7	2:8	1:9
EAC:CYH	25	30	50	100	50	30	50	30	50
DCM:CYH	50	50	100	PG	PG	PG	PG	P	P