Anthraquinone-based extended dendritic monomers: electrochemical comparisons

Abstract

The anthraquinonoid 1→3 branched monomer 5, possessing a simple urea linkage, affords a direct synthesis of electroactive, dendritic monomers. Exploratory cyclic voltammetry (CV) experiments of monomer 5 and the related alkyl and aryl counterparts suggest avenues to dendrimers featuring tunable electrochemical potentials based on anthraquinones.

Dendrimers Derived from 1 → 3 Branching Motifs

“…The use of more rigid spacer units between branching centers and the redox sites via the use of aryl diacyl chlorides has also been examined, along with the attendant electrochemistry . The electrochemical comparison of these anthraquinoid architectures has been reported . The incorporation of N , N ′-bis(3-aminopropyl)piperazine ( 86 ) was accomplished by its treatment with 76 and Behera’s amine to generate the 1:1:1 (20%; 87 ) and the two-directional 1:2:2 ( 88 ) dendrimers (Scheme ).…”

“…By using application-oriented monomers, Newkome et al [508][509][510] created anthraquinone-based, 508 redox-active dendrimers (Scheme 21). Synthesis of the functionalized monomers was achieved via a three-component, single-pot reaction using glutaryl dichloride (76), amine 40, and 1,4-diaminoanthraquinone (82) to give the homologated aminotriester 83.…”

“…512 The electrochemical comparison of these anthraquinoid architectures has been reported. 510 The incorporation of N,N′-bis(3-aminopropyl)piperazine (86) was accomplished by its treatment with 76 and Behera's amine to generate the 1:1:1 (20%; 87) and the two-directional 1:2:2 (88) dendrimers (Scheme 22). Reaction of the functionalized dendron 87 with the tetraacid chloride 79 gave the appropriate four-directional dendrimer 89, which was transformed to the G2 product by hydrolysis, and subsequent treatment with excess Behera's amine.…”