Multifunctional triazolylferrocenyl Janus dendron: Nanoparticle stabilizer, smart drug carrier and supramolecular nanoreactor

Abstract

Owing to their unique broken symmetry, amphiphilic Janus dendrimers and dendons provide fascinating properties for material, biological, pharmaceutical and biomedical applications. The integration of various organometallic moieties into these macromolecules will further offer the opportunity to form complex and intelligent architectures and materials. Here, we report a novel, simple and multifunctional Janus dendron containing redox‐reversible hydrophobic ferrocene (Fc) unit, complexing‐effective 1,2,3‐triazole ligand and biocompatible hydrophilic triethylene glycol termini. Silver and gold nanoparticles were firstly successfully prepared by using the Janus dendron as the reducing agent of Au(III) and Ag(I), and the stabilizer of the corresponding nanoparticles. The redox response of the Fc moiety was then employed to trigger the release of model drug, rhodamine B, encapsulated in supramolecular micelles formed by the self‐assembly of the Janus dendron. Finally, the precise and excellent metal‐complexing ability of the triazole group in this dendron was fully utilized to stabilize a water‐soluble Cu(I) catalyst, forming supramolecular nanoreactors for the catalysis of the copper(I)‐catalyzed azide alkyne cycloaddition click reaction in only water. The multifunctional characteristics of this dendron highlight the potential for organometallic Janus dendrimers and dendrons in the fields of functional materials and nanomedicines.

Ferrocenyl amphiphilic Janus dendrimers as redox‐responsive micellar carriers

“…[2,3] The UV-visible spectroscopy further provides powerful proof for the transformation of Fc groups into Fcium cations. [2,3] Subsequently, ascorbic acid was added stoichiometrically to reduce the green Fcium-containing JD. And after the addition of Fe 2 (SO 4 ) 3 , this characteristic peak disappears, and an emerging absorption band at 630 nm is attributed to the characteristic Fcium moieties.…”

“…[1][2][3] and are attracting wide attention owing to their combination of properties of the constituting blocks in a unique way. [1][2][3] and are attracting wide attention owing to their combination of properties of the constituting blocks in a unique way.…”

“…The azido derivative 4 [3] and azidomethylferrocene 6 [2] were synthesized according to the known procedures. The azido derivative 4 [3] and azidomethylferrocene 6 [2] were synthesized according to the known procedures.…”

Supramolecular redox-responsive substrate carrier activity of a ferrocenyl Janus device

“…They have recently attracted the specific attention of scientists in various research fields including macromolecular chemistry [1], molecular materials [2,3] and biomedicine [4]. The reported Janus derivatives were innovatively applied in various fields such as thermal actuators [5], ionic liquids [6], catalysis [7], light capture [8], bioimaging [9], optoelectronics [10,11] and drug delivery [12][13][14][15][16]. Unlike conventional symmetric molecules [17], Janus molecules are normally constructed using two distinct hemispheres with different sizes and functionalities, featuring asymmetric structures [1][2][3][4].…”

Fabrication of Ternary Hybrid Colloids via In‐Situ Polymerization at the Interface of Oil/Water Emulsion

“…Because of their special morphology and composition, these asymmetric colloids have shown great promise in drug delivery, [6– catalyst, [9– self‐propelled nanomotors, [12– surfactants, [15, and forth. [17, Progress in nanotechnology has made it possible to construct numerous asymmetric colloids with different functionalities. The methods to fabricate the asymmetric colloids are generally divided into four categories, interface protection, [19– phase separation, [23– self‐assembly, [26– and surface nucleation and growth.…”