Facile access to internally functionalized dendrimers through efficient and orthogonal click reactions

Abstract

A simple synthetic strategy has been developed for accessing internally functionalized dendrimers. The key feature of this approach is the use of two orthogonal and efficient reactions--'epoxy-amine' and 'thiol-ene' coupling--for rapid growth of the dendritic scaffold. This sequence of reactions allows for the introduction of reactive hydroxyl groups at each dendritic layer.

Mussel-Inspired Anchoring of Polymer Loops That Provide Superior Surface Lubrication and Antifouling Properties

“…The prepared silyl-protected catecholic monomer ( 5 ) was then used to functionalize the P(EO- co -AGE)- b -PEO- b -P(EO- co -AGE) triblock copolymers ( 9 ) through a simple thiol–ene reaction by exposure to 365 nm light for 30 min in the presence of 2,2-dimethoxy-2-phenylacetophenone as a photochemical initiator. 21 The silyl-protected catechol-functionalized triblock copolymer ( 8 ) was obtained in quantitative yield without any observable silyl deprotection or allyl groups remaining.…”

DendriPeps: Expanding Dendrimer Functionality by Hybridizing Poly(amidoamine) (PAMAM) Scaffolds with Peptide Segments

“…Yet, the design of their chemically inert backbone has remained unaltered for three decades . In fact, the internal structure of nearly every class of dendrimers presented to date does not exhibit any functional groups other than the branch termini, exception made for a few examples . Developing a modular method to furnish internally functionalized dendrimers offers a tremendous opportunity to advance dendrimer chemistry and unlock their full potential in the biomedical field.…”

Synthesis of carbosilane dendrons and dendrimers derived from 1,3,5-trihydroxybenzene

“…Method (B): Reaction of 25 (1.00 g, 0.95 mmol) and C 3 H 5 N(C 2 H 4 CO 2 Me) 2 (1.44 g, 6.08 mmol) in THF (5 mL) in the presence of Karstedt's catalyst (3% mol) was stirred overnight at 40 C. Next, THF was added (15 mL), the solution was filtered through active carbon and the volatiles were removed under vacuum. The remaining oil was washed with cold hexane (10 mL) obtaining compound 19 as a pale yellow oil (2.14 g, 91% 48 (21). Method (B): Following the procedure described for compound 19 (method B), compound 21 was obtained as a pale yellow oil (0.31 g, 88%) from the reaction of 26 12 (23).…”