Preparation of a Redox-Gradient Dendrimer. Polyamines Designed for One-Way Electron Transfer and Charge Capture

Selby, Trent D.; Blackstock, Silas C.

doi:10.1021/ja9821091

Cited by 96 publications

(49 citation statements)

References 16 publications

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“…[24] Both Cu-and Pdcatalysed aminations have been used by Blackstock et al to construct dendritic poly(arylamine)s with interesting redox chemistry. [25] Herein, we report our studies on the effects of introducing modifications into the p-conjugated backbone of Ph/Ph TANI by using the Buchwald-Hartwig cross-coupling strategy. Focusing on Ph/Ph TANI, and choosing to examine the effect of varying the nature of the central ring, has allowed us to take advantage of the symmetrical molecular architecture of this species to produce a novel range of derivatives with a modified central aromatic core.…”

Section: Ature It Was Only From 1984 Onwards That the Simultaneous mentioning

confidence: 99%

Delineating Poly(Aniline) Redox Chemistry by Using Tailored Oligo(Aryleneamine)s: Towards Oligo(Aniline)‐Based Organic Semiconductors with Tunable Optoelectronic Properties

Shao

Rannou

Sadki

et al. 2011

Chemistry A European J

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The simple and elegant Buchwald-Hartwig cross-coupling reaction has been used to synthesise a designed range of new aniline-based tetramers in one step, and without the need for protecting groups. Variation of the central aromatic ring has provided the opportunity to carefully tune the optoelectronic properties in this series, thus enabling a structure-activity relationship study by using a range of photophysical and electrochemical techniques. As a result, the long-proposed sequences of electron-electron (EE) and electron-chemical (EC) processes that support the complex redox and proton-transfer reactions involved in the well-known switching of redox states of poly- and oligo(aniline)s are revealed here for the first time. We also present the initial results from time-dependent DFT calculations to clarify the optoelectronic behaviour of these oligomers. The dc-conductivity measurements of conducting thin films of this series, doped with the prototypical poly(aniline) protonating agent D,L-camphor-10-sulfonic acid (CSA), externally plasticised with triphenyl phosphate (TPP), and processed from m-cresol (MC) solutions, are also presented.

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Section: Ature It Was Only From 1984 Onwards That the Simultaneous mentioning

confidence: 99%

Delineating Poly(Aniline) Redox Chemistry by Using Tailored Oligo(Aryleneamine)s: Towards Oligo(Aniline)‐Based Organic Semiconductors with Tunable Optoelectronic Properties

Shao

Rannou

Sadki

et al. 2011

Chemistry A European J

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“…[8±11] The resulting dendritic effects concern redox protein mimetics, [3] redox gradients, [11] charge transfer (CT) complex-based conductivity, [7] electron sponges, [4] and redox sensors. [12] We present here a new homologous series of electroactive dendrimers belonging to class (c).…”

Section: Generation-dependent Intramolecular Ct Complexation In a Denmentioning

confidence: 99%

“…The dramatic color change upon electrooxidation of OMT can also be achieved by a variety of chemical oxidants such as aromatic radical cations, [8] nitrosonium cation, [9] or triethyloxonium hexachloroantimonate. [10] For example, a blue solution of a octahydronaphthacene radical cation [11] …”

mentioning

confidence: 99%

Generation-Dependent Intramolecular CT Complexation in a Dendrimer Electron Sponge Consisting of a Viologen Skeleton

Heinen

Walder

2000

Angew. Chem. Int. Ed.

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“…72 Monomer 22 was readily available because methyl gallate could be selectively deprotonated and, therefore, allylated on account of the higher acidity of the 4-hydroxy group. All eight different combinations of inner dendrons 24-27 and outer dendrons 28-31 were prepared and then combined with a double-stage convergent growth approach [73][74][75] to afford a total of 16 fourthgeneration dendron structures (32)(33)(34)(35)(36)(37)(38)(39)(40)(41)(42)(43)(44)(45)(46)(47). Methyl benzoates, rather than benzylic alcohols, were used for growth because alkylations proceed with higher degrees of regioselectivity, i.e., no O-alkylation is observed, and the additional reduction step is facilitated by workup with Baeckström's reagent.…”

Section: Aromatic Backbonesmentioning

confidence: 99%

Functionalizing the interior of dendrimers: Synthetic challenges and applications

Hecht

2003

J. Polym. Sci. A Polym. Chem.

119

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Chemists' fascination with dendrimers mainly originates from their unique architecture and its exploitation for the design of well‐defined functional macromolecules. Depending on the nature of the synthesis, functionalization is traditionally introduced at the core, the periphery, or both. However, the specific incorporation of functional groups at the interior layers, i.e., generations, represents a considerable synthetic hurdle that must be overcome for the full potential of dendrimers to be realized. This review covers recent advances in this emerging frontier of dendrimer science with a particular focus on covalent modifications. Monomer design, syntheses, and properties of various dendritic backbone types are discussed. Internal functionalization dramatically increases the degree of complexity that can be implemented into a dendrimer macromolecule and, therefore, promises to lead to smart materials for future applications in bio‐ and nanotechnologies. © 2003 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 41: 1047–1058, 2003

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Preparation of a Redox-Gradient Dendrimer. Polyamines Designed for One-Way Electron Transfer and Charge Capture

Cited by 96 publications

References 16 publications

Delineating Poly(Aniline) Redox Chemistry by Using Tailored Oligo(Aryleneamine)s: Towards Oligo(Aniline)‐Based Organic Semiconductors with Tunable Optoelectronic Properties

Delineating Poly(Aniline) Redox Chemistry by Using Tailored Oligo(Aryleneamine)s: Towards Oligo(Aniline)‐Based Organic Semiconductors with Tunable Optoelectronic Properties

Generation-Dependent Intramolecular CT Complexation in a Dendrimer Electron Sponge Consisting of a Viologen Skeleton

Functionalizing the interior of dendrimers: Synthetic challenges and applications

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