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Review
. 2020 Dec 15;12(12):2987.
doi: 10.3390/polym12122987.

Sulfonimide-Based Dendrimers: Progress in Synthesis, Characterization, and Potential Applications

Julia V Bondareva  1 , Stanislav A Evlashin  1 , Oleg V Lukin  2
Affiliations
Review

Sulfonimide-Based Dendrimers: Progress in Synthesis, Characterization, and Potential Applications

Julia V Bondareva et al. Polymers (Basel). .

Abstract

There are more than 50 families of dendrimers, and some of which, such as polyamidoamine PAMAM, are well studied, and some are just starting to attract the attention of researchers. One promising type of dendrimers is sulfonimide-based dendrimers (SBDs). To date, SBDs are used in organic synthesis as starting reagents for the convergent synthesis of higher generations dendrimers, in materials science as alternative electrolyte solutions for fuel cells, and in medicinal chemistry as potential substances for drug transfer procedures. Despite the fact that most dendrimers are amorphous substances among the SBDs, several structures are distinguished that are prone to the formation of crystalline solids with melting points in the range of 120-250 °C. Similar to those of other dendrimers, the chemical and physical properties of SBDs depend on their outer shell, which is formed by functional groups. To date, SBDs decorated with end groups such as naphthyl, nitro, methyl, and methoxy have been successfully synthesized, and each of these groups gives the dendrimers specific properties. Analysis of the structure of SBD, their synthesis methods, and applications currently available in the literature reveals that these dendrimers have not yet been fully explored.

Keywords: dendrimers; dendritic polymers; dendrons; divergent approach; functionalization; generations; sulfonimide.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
The number of publications related to dendrimers and sulfonimide-based dendrimers (SBDs) according to Scopus 1990–2020.
Figure 2
Figure 2
(a) Schematic of the dendrimer structure showing the key components. (b) A schematic of a G1 of SBD in the form of a planar graph.
Figure 3
Figure 3
The dependence of contact angle on the number of naphthyl terminal groups in the dendrimer structure.
Figure 4
Figure 4
(a) Planar representation of a G3 SBD and its 3D architecture with a Connolly molecular surface. (b) Planar representation of a G4 SBD and its 3D architecture with a Connolly molecular surface.
Scheme 1
Scheme 1
Controllable per-functionalization (persulfonylation) of dendritic oligoamines.
Scheme 2
Scheme 2
Persulfonylation of a G1 polypropylene-amine (POPAM) dendrimer.
Scheme 3
Scheme 3
Synthesis of symmetrical oligo SBD (a) NO2C6H4SO2Cl, Et3N, CH2Cl2, reflux; (b) H2, 10% Pd/C, C6H6/C2H5OH (c) CH3C6H4SO2Cl, Et3N, CH2Cl2, reflux.
Scheme 4
Scheme 4
Synthesis of SBDs with structural asymmetry. (a) 4-NO2C6H4SO2Cl, Et3N, CH2Cl2 (b) SnCl2, HCl, EtOH, reflux; (c) CH3C6H4SO2Cl, Et3N, CH2Cl2, reflux.
Scheme 5
Scheme 5
Synthesis of macromonomers MG1 and MG2. (a) ArSO2Cl, Et3N, CH2Cl2 (b) diisobutylaluminum hydride (DIBAL-H), tetrahydrofuran (THF) (c) SnCl2/HCl, EtOH: dichloromethane (DCM); (d) MAC, trimethylamine (TEA), THF.
Scheme 6
Scheme 6
Synthesis of a terphenyl-cored SBDs using 1,4-phenylene diboronic acid diester, Pd[(P(pTol)3]3, THF/H2O.
Scheme 7
Scheme 7
Synthesis of bis-sulfonyl chloride. (a) benzyl mercaptan, K2CO3, DMF (b) SnCl2, i-PrOH (c) CH3C6H4SO2Cl, Et3N, CH2Cl2 (d) N-chlorosuccinimide, HCl, CH3COOH.
Scheme 8
Scheme 8
Synthesis of persulfonylated azide-functionalized dendron and the convergent synthesis of persulfonylated G1 dendrimers.
Scheme 9
Scheme 9
Synthesis of mixed sulfonimide and sulfonamide derivatives.
Scheme 10
Scheme 10
The synthesis of mixed sulfonimide and sulfonamide derivatives with different functionalities.
Scheme 11
Scheme 11
The synthesis of a dumbbell-shaped dendrimer by a convergent method.
Scheme 12
Scheme 12
Partial removal of the branches from naphthyl-decorated dendron by the action of a phenolate nucleophile.
Scheme 13
Scheme 13
Selective removal of one peripheral group from G2 dendron.
Scheme 14
Scheme 14
Selective removal of one peripheral group from G3 dendron.
Figure 5
Figure 5
Application of SBDs according to the nature of functional groups and branching points.
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References

    1. Ratner B.D., Hoffman A.S., Schoen F.J., Lemons J.E. Biomaterials Science. Elsevier; Amsterdam, The Netherlands: 2013.
    1. Liu X., Gregurec D., Irigoyen J., Martinez A., Moya S., Ciganda R., Hermange P., Ruiz J., Astruc D. Precise localization of metal nanoparticles in dendrimer nanosnakes or inner periphery and consequences in catalysis. Nat. Commun. 2016;7:1–8. doi: 10.1038/ncomms13152. - DOI - PMC - PubMed
    1. Walter M.V., Malkoch M. Simplifying the synthesis of dendrimers: Accelerated approaches. Chem. Soc. Rev. 2012;41:4593–4609. doi: 10.1039/c2cs35062a. - DOI - PubMed
    1. McCarthy T.D., Karellas P., Henderson S.A., Giannis M., O’Keefe D.F., Heery G., Paull J.R.A., Matthews B.R., Holan G. Dendrimers as drugs: Discovery and preclinical and clinical development of dendrimer-based microbicides for HIV and STI prevention. Mol. Pharm. 2005;2:312–318. doi: 10.1021/mp050023q. - DOI - PubMed
    1. Madaan K., Kumar S., Poonia N., Lather V., Pandita D. Dendrimers in drug delivery and targeting: Drug-dendrimer interactions and toxicity issues. J. Pharm. Bioallied Sci. 2014;6:139–150. doi: 10.4103/0975-7406.130965. - DOI - PMC - PubMed

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