Synthesis and Properties of Photoresponsive Organogels Based on Azobenzene Derivatives

doi:10.7503/cjcu20140195

Abstract

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

CLC Number:

O648.17

TrendMD:

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

Figures/Tables 8

References 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