Heterofunctionalized Carbosilane Dendritic Systems: Bifunctionalized Dendrons as Building Blocks versus Statistically Decorated Dendrimers

Abstract

Click" chemistry based on thiol−ene synthetic protocols has been used to successfully bifunctionalize anionic carbosilane dendritic structures in two effective ways. The first consists of the formation of statistically heterofunctionalized dendrimers, the second being the synthesis of heterofunctionalized dendrons. Regarding the latter approach, a versatile and simple procedure has been developed for the synthesis of a library of anionic carbosilane dendrons. Taking into account the chemical diversity at the focal point for both neutral-and anionic-terminated dendrons, such as azide, alcohol, amine, bromine, carboxylic acid, and alkyne, these dendritic systems may act as building blocks to give more original dendritic architectures.

Dendronized Anionic Gold Nanoparticles: Synthesis, Characterization, and Antiviral Activity

“…However, one disadvantage of dendrimers is the usually high number of synthetic steps required for their production, especially if high‐generation derivatives are required. This drawback is remarkable in compound 2G‐SF16 and other synthetic strategies have been employed to facilitate the preparation of anionic systems, such as thiol‐ene addition . The compounds thus obtained showed also important anti‐HIV properties .…”

“…This drawback is remarkable in compound 2G-SF16 and other synthetic strategies have been employed to facilitatet he preparation of anionic systems, such as thiol-ene addition. [36] The compounds thus obtained showeda lso important anti-HIV properties. [35] Furthermore, the thiol-ene approach provedi ts value in the synthesis of dendrons.…”

“…The compounds thus obtained showed also important anti‐HIV properties . Furthermore, the thiol‐ene approach proved its value in the synthesis of dendrons …”

“…[35] Furthermore, the thiol-ene approach provedi ts value in the synthesis of dendrons. [36] Dendrons are molecules similart od endrimers with analogous properties, but instead of presenting spherical shapes they are cone-shaped with two different functions:t he focal point and dendron surface. Whereast he dendron surface has the same functional design as dendrimers, the focal point can be used as an anchor, [37] form odifying the properties of polymers, [38] for stabilizing NPs, [39][40][41][42][43] for improvingthe biological activity of functional molecules, [44][45][46][47] and for other purposes.…”

Fluorescein labelled cationic carbosilane dendritic systems for biological studies

“…In both cases, the synthesis was performed from compounds containing one -NH 2 group and several -NMe 2 functions, employing the typical addition of a -NH 2 moiety to the isothiocyanate function of modified FITC (5 0 -isothiocyanatefluorescein) and the quaternization with MeI of dimethylamino (-NMe 2 ) peripheral groups. The amine groups on the periphery of carbosilane dendrimers and dendrons were introduced by thiol-ene click chemistry, which is a simple procedure to achieve this goal in carbosilane dendritic molecules with high yields [57][58][59][60]. The reaction of vinyl dendrimers GnO 3 V m (n = 1, m = 6; n = 2, m = 12; n = 3, m = 24) [59] with one equivalent of cysteamine hydrochloride HS(CH 2 ) 2 NH 3 Cl, under UV irradiation, enabled the introduction of one of these functions on the periphery of dendrimers (Scheme 1).…”