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Review
. 2022 Feb 4;23(3):1798.
doi: 10.3390/ijms23031798.

Gemini and Bicephalous Surfactants: A Review on Their Synthesis, Micelle Formation, and Uses

Lluvia Guerrero-Hernández  1 , Héctor Iván Meléndez-Ortiz  2 , Gladis Y Cortez-Mazatan  1 , Sandra Vaillant-Sánchez  1 , René D Peralta-Rodríguez  1
Affiliations
Review

Gemini and Bicephalous Surfactants: A Review on Their Synthesis, Micelle Formation, and Uses

Lluvia Guerrero-Hernández et al. Int J Mol Sci. .

Abstract

The use of surfactants in polymerization reactions is particularly important, mainly in emulsion polymerizations. Further, micelles from biocompatible surfactants find use in pharmaceutical dosage forms. This paper reviews recent developments in the synthesis of novel gemini and bicephalous surfactants, micelle formation, and their applications in polymer and nanoparticle synthesis, oil recovery, catalysis, corrosion, protein binding, and biomedical area, particularly in drug delivery.

Keywords: amphiphiles; bicephalous surfactants; drug nanocarriers; gemini surfactants; micelles; polymer.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Schematic representation of the different types of surfactants.
Figure 2
Figure 2
Chemical structures of some anionic surfactants.
Figure 3
Figure 3
Examples of some common cationic surfactants.
Figure 4
Figure 4
Chemical structures of common non-ionic surfactants.
Figure 5
Figure 5
Chemical structures of some zwitterionic surfactants.
Figure 6
Figure 6
Schematic representation of different types of micelles.
Figure 7
Figure 7
Typical structures of gemini surfactants.
Figure 8
Figure 8
Representation of micelles formed from (a) conventional surfactants and (b) gemini surfactants.
Figure 9
Figure 9
Schematic representation of the different types of gemini surfactants: (a) flexible spacer, (b) rigid spacer, (c) short chain spacer, (d) long-chain spacer, (e) polar spacer, (f) cationic, (g) anionic, (h) zwitterionic, (i) non-ionic, (j) two identical hydrophilic heads and hydrophobic chains, (k) two non-identical hydrophobic chains, and (l) two non-identical hydrophilic heads.
Figure 10
Figure 10
Geometries of micelles from gemini surfactants linked by the tail: (a) fiber-like, (b) elliptical, and (c) spherical.
Figure 11
Figure 11
General routes to obtain gemini surfactants. (a) Reaction of long chain tertiary amines with dihalogenated substrates as organic di-bromides or dichlorides; (b) reaction of N,N,N′,N′-tetramethylpolymethylene diamines with alkyl halides; and (c) reaction of long chain tertiary amines with a haloalkylene oxide substrate.
Figure 12
Figure 12
Route of synthesis of the imidazolium gemini surfactants synthesized by Ren et al. [85].
Figure 13
Figure 13
Synthesis of sulfonate gemini surfactants.
Figure 14
Figure 14
Synthesis of gemini surfactants containing an ester group.
Figure 15
Figure 15
Scheme of transition from micelles to vesicles and vice versa.
Figure 16
Figure 16
(a) Anionic gemini surfactant derived from cysteine and (b) its monomeric counterpart; (c) chemical structure of antifungal polyene antibiotic amphotericin B.
Figure 17
Figure 17
Chemical structures of some gemini surfactants used as corrosion inhibitors.
Figure 18
Figure 18
Schematic representations of (a) a bicephalous dicationic surfactant; and (b) a bicephalous dianionic surfactant.
Figure 19
Figure 19
Synthesis of bicephalous dianionic surfactant proposed by Kalhapure et al. [147].
Figure 20
Figure 20
Synthesis of bicephalous dianionic surfactant proposed by Ojewole et al. [148].
Figure 21
Figure 21
Synthesis of bicephalous dianionic surfactants proposed by Chaudhari et al. [150].
Figure 22
Figure 22
Synthesis of the bicephalous cationic surfactants proposed by Hassan et al. [151].
Figure 23
Figure 23
Chemical structures of some bicephalous surfactants reported in recent years.
Figure 24
Figure 24
Micelle structure from (a) a conventional surfactant; and (b) a bicephalous surfactant.
See this image and copyright information in PMC

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