Structure-property correlation of a new family of organogelators based on organic salts and their selective gelation of oil from oil/water mixtures

Trivedi, Darshak R. ; Ballabh, Amar ; Dastidar, Parthasarathi ; Ganguly, Bishwajit (2004) Structure-property correlation of a new family of organogelators based on organic salts and their selective gelation of oil from oil/water mixtures Chemistry - A European Journal, 10 (21). pp. 5311-5322. ISSN 0947-6539

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/chem.20...

Related URL: http://dx.doi.org/10.1002/chem.200400122

Abstract

Organic salts based on dicyclohexylamine and substituted/unsubstituted cinnamic acid exhibit efficient gelation of organic fluids, including selective gelation of oil from an oil/water mixture. Among the cinnamate salts, dicyclohexylammonium 4-chlorocinnamate (1), 3-chlorocinnamate (2), 4-bromocinnamate (3), 3-bromocinnamate (4), 4-methylcinnamate (5) and the parent cinnamate (6) are gelators, whereas 2-chlorocinnamate (7), 2-bromocinnamate (8), 3-methylcinnamate (9), 2-methylcinnamate (10) and hydrocinnamate (11) are non-gelators. Non-gelation behaviour of 11 and various benzoate derivatives 12–18 indicate the significance of an unsaturated backbone in the gelation behaviour of the cinnamate salts. A structure–property correlation based on the single-crystal structures of most of the gelators (1, 3, 5 and 6) and non-gelators, such as 7, 8, 10–18, indicates that the prerequisite for the one-dimensional (1D) growth of the gel fibrils is mainly governed by the 1D hydrogen-bonded network involving the ion pair. All the non-gelators show either two- (2D) or zero-dimensional (0D) hydrogen-bonded assemblies involving the ion pair. The molecular packing of the fibres in the xerogels of 1, 3, 5 and 6 has also been established on the basis of their simulated powder diffraction patterns, XRPD of bulk solids and xerogels. Ab initio quantum chemical calculations suggests that π–π interactions is not a contributing factor in the gelation process.

Item Type:Article
Source:Copyright of this article belongs to John Wiley & Sons, Inc.
Keywords:Ab Initio Calculations; Aggregation; Gels; Hydrogen Bonds; Self-Assembly; Structure–Property Relationship
ID Code:112682
Deposited On:19 Apr 2018 10:17
Last Modified:19 Apr 2018 10:17

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