|
|
|
| To gel or not to gel: A prior prediction of gelation in solvent mixtures |
| Peng Lina,b, Nan-Xiang Zhanga,b, Jing-Jing Lia, Jing Zhangc, Jia-Hui Liua, Bao Zhanga,d, Jian Songa,b,d |
a School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350, China;
b The Co-Innovation Center of Chemistry and Chemical Engineering of Tianjin, Tianjin 300072, China;
c Renai College of Tianjin University, Tianjin 301636, China;
d Tianjin Engineering Research Center of Functional Fine Chemicals, Tianjin 300072, China |
|
|
|
|
Abstract The gelation behaviours of low molecular weight gelators 1,3:2,5:4,6-tris(3,4-dichlorobenzylidene)-D-mannitol(G1)and 2,4-(3,4-dichlorobenzylidene)-N-(3-aminopropyl)-D-gluconamide(G2)in 34 solvents have been studied.We found that sample dissolved at low concentrations may become a gel or precipitate at higher concentrations.The Hansen solubility parameters(HSPs)and a Teas plot were employed to correlate the gelation behaviours with solvent properties,but with no success if the concentration of the tests was not maintained constant.Instead,on the basis of the gelation results obtained for the G1 and G2 in single solvents,we studied the gelation behaviours of G1 and G2 in 23 solvent mixtures and found that the tendency of a gelator to form a gel in mixed solvents is strongly correlated with its gelation behaviours in good solvents.If the gelation occurs in a good solvent at higher concentrations,it will take place as well in a mixed solvent(the good solvent plus a poor solvent)at a certain volume ratio.In contrast,if the gelator forms a precipitate in a good solvent at higher concentrations,no gelation is to be observed in the mixed solvents.A gelation rule for mixed solvents is thus proposed,which may facilitate decision making with regard to solvent selection for gel formation in the solvent mixtures in practical applications.
|
|
Received: 14 November 2016
Published: 07 January 2017
|
| Fund:We are grateful for the financial support of the National Natural Science Foundation of China(Nos.21276188,21476164)and Tianjin Science and Technology Innovation Platform Program(No. 14TXGCCX00017). |
|
Corresponding Authors:
Bao Zhang, Jian Song
E-mail: baozhang@tju.edu.cn;songjian@tju.edu.cn
|
|
|
|
| [1] |
Y.Lan,M.G.Corradini,R.G.Weiss,S.R.Raghavan,M.A.Rogers,To gel or not to gel:correlating molecular gelation with solvent parameters,Chem.Soc.Rev. 44(2015)6035-6058.
|
| [2] |
P.Terech,R.G.Weiss,Low molecular mass gelators of organic liquids and the properties of their gels,Chem.Rev.97(1997)3133-3160.
|
| [3] |
S.S.Babu,V.K.Praveen,A.Ajayaghosh,Functional p-gelators and their applications,Chem.Rev.114(2014)1973-2129.
|
| [4] |
G.C.Yu,X.Z.Yan,C.Y.Han,F.H.Huang,Characterization of supramolecular gels, Chem.Soc.Rev.42(2013)6697-6722.
|
| [5] |
M.O.M.Piepenbrock,G.O.Lloyd,N.Clarke,J.W.Steed,Metal-and anion-binding supramolecular gels,Chem.Rev.110(2010)1960-2004.
|
| [6] |
D.K.Smith,Lost in translation? Chirality effects in the self-assembly of nanostructured gel-phase materials,Chem.Soc.Rev.38(2009)684-694.
|
| [7] |
J.W.Steed,Anion-tuned supramolecular gels:a natural evolution from urea supramolecular chemistry,Chem.Soc.Rev.39(2010)3686-3699.
|
| [8] |
K.J.C.van Bommel,A.Friggeri,S.Shinkai,Organic templates for the generation of inorganic materials,Angew.Chem.Int.Ed.42(2003)980-999.
|
| [9] |
Y.Liang,L.M.Tang,Y.Xia,et al.,One-pot synthesis of network supported catalyst using supramolecular gel as template,Chin.Chem.Lett.21(2010) 991-994.
|
| [10] |
W.Zhang,Z.G.Xie,Fabrication of palladium nanoparticles as effective catalysts by using supramolecular gels,Chin.Chem.Lett.27(2016)77-80.
|
| [11] |
Y.Gao,Y.Kuang,Z.F.Guo,et al.,Enzyme-instructed molecular self-assembly confers nanofibers and a supramolecular hydrogel of taxol derivative,J.Am. Chem.Soc.131(2009)13576-13577.
|
| [12] |
S.Bhattacharya,S.K.Samanta,Soft functional materials induced by fibrillar networks of small molecular photochromic gelators,Langmuir 25(2009) 8378-8381.
|
| [13] |
B.Escuder,M.L.Lusar,J.F.Miravet,Insight on the NMR study of supramolecular gels and its application to monitor molecular recognition on self-assembled fibers,J.Org.Chem.71(2006)7747-7752.
|
| [14] |
A.Prathap,K.M.Sureshan,A mannitol based phase selective supergelator offers a simple,viable and greener method to combat marine oil spills,Chem. Commun.48(2012)5250-5252.
|
| [15] |
A.M.Vibhute,V.Muvvala,K.M.Sureshan,A sugar-based gelator for marine oil-spill recovery,Angew.Chem.Int.Ed.55(2016)7782-7785.
|
| [16] |
M.Luo,S.Wang,M.L.Wang,et al.,Novel organogel harnessing excited-state intramolecular proton transfer process with aggregation induced emission and photochromism,Dyes Pigm.132(2016)48-57.
|
| [17] |
B.Isare,L.Petit,E.Bugnet,et al.,The weak help the strong:low-molar-mass organogelators harden bitumen,Langmuir 25(2009)8400-8403.
|
| [18] |
R.G.Weiss,The past present,and future of molecular gels.What is the status of the field,and where is it going,J.Am.Chem.Soc.136(2014)7519-7530.
|
| [19] |
M.Bielejewski,A.?apiński,R.Luboradzki,J.Tritt-Goc,Solvent effect on 1,2-O-(1-Ethylpropylidene)-a-D-glucofuranose organogel properties,Langmuir 25 (2009)8274-8279.
|
| [20] |
A.R.Hirst,D.K.Smith,Solvent effects on supramolecular gel-phase materials: two-component dendritic gel,Langmuir 20(2004)10851-10857.
|
| [21] |
G.Y.Zhu,J.S.Dordick,Solvent effect on organogel formation by low molecular weight molecules,Chem.Mater.18(2006)5988-5995.
|
| [22] |
K.Q.Fan,L.B.Niu,J.Q.Li,et al.,Application of solubility theory in bi-component hydrogels of melamine with di(2-ethylhexyl)phosphoric acid,Soft Matter 9 (2013)3057-3062.
|
| [23] |
C.Q.Tong,K.Q.Fan,L.B.Niu,et al.,Application of solubility parameters in a D-sorbitol-based organogel in binary organic mixtures,Soft Matter 10(2014) 767-772.
|
| [24] |
W.Edwards,C.A.Lagadec,D.K.Smith,Solvent-gelator interactions-using empirical solvent parameters to better understand the self-assembly of gel-phase materials,Soft Matter 7(2011)110-117.
|
| [25] |
W.Edwards,D.K.Smith,Dynamic evolving two-component supramolecular gels—hierarchical control over component selection in complex mixtures,J. Am.Chem.Soc.135(2013)5911-5920.
|
| [26] |
S.Wu,J.Gao,T.J.Emge,M.A.Rogers,Influence of solvent on the supramolecular architectures in molecular gels,Soft Matter 9(2013)5942-5950.
|
| [27] |
J.Bonnet,G.Suissa,M.Raynal,L.Bouteiller,Organogel formation rationalized by Hansen solubility parameters:dos and don'ts,Soft Matter 10(2014) 3154-3160.
|
| [28] |
Y.Q.Lan,M.G.Corradini,X.Liu,et al.,Comparing and correlating solubility parameters governing the self-assembly of molecular gels using 1,3:2,4-dibenzylidene Sorbitol as the gelator,Langmuir 30(2014)14128-14142.
|
| [29] |
N.Yan,Z.Y.Xu,K.K.Diehn,et al.,Pyrenyl-linker-glucono gelators.Correlations of gel properties with gelator structures and characterization of solvent effects,Langmuir 29(2013)793-805.
|
| [30] |
J.Gao,S.Wu,M.A.Rogers,Harnessing hansen solubility parameters to predict organogel formation,J.Mater.Chem.22(2012)12651-12658.
|
| [31] |
M.Raynal,L.Bouteiller,Organogel formation rationalized by Hansen solubility parameters,Chem.Commun.47(2011)8271-8273.
|
| [32] |
H.Q.Xu,J.Song,T.Tian,R.X.Feng,Estimation of organogel formation and influence of solvent viscosity and molecular size on gel properties and aggregate structures,Soft Matter 8(2012)3478-3486.
|
| [33] |
K.K.Diehn,H.Oh,R.Hashemipour,R.G.Weiss,S.R.Raghavan,Insights into organogelation and its kinetics from Hansen solubility parameters.Toward a priori predictions of molecular gelation,Soft Matter 10(2014)2632-2640.
|
| [34] |
N.Yan,Z.Y.Xu,K.K.Diehn,et al.,How do liquid mixtures solubilize insoluble gelators? Self-assembly properties of pyrenyl-linker-glucono gelators in tetrahydrofuran-water mixtures,J.Am.Chem.Soc.135(2013)8989-8999.
|
| [35] |
J.Bonnet,G.Suissa,M.Raynal,L.Bouteiller,Organogel formation rationalized by Hansen solubility parameters:influence of gelator structure,Soft Matter 11 (2015)2308-2312.
|
| [36] |
H.H.Shen,L.B.Niu,K.Q.Fan,et al.,Application of solubility parameters in 1,3:2,4-bis(3,4-dimethylbenzylidene)sorbitol organogel in binary organic mixtures,Langmuir 30(2014)9176-9182.
|
| [37] |
X.X.Zhang,P.F.Deng,R.X.Feng,J.Song,Novel gelatinous shape-stabilized phase change materials with high heat storage density,Sol.Energy Mater.Sol. Cells 95(2011)1213-1218.
|
| [38] |
H.Koshima,W.Matsusaka,H.Yu,Preparation and photoreaction of organogels based on benzophenone,J.Photochem.Photobiol.A Chem.156(2003)83-90.
|
|
|
|
