Metal-promoted C1 polymerizations

Cahoon, Collin; Bielawski, Christopher W.

doi:10.1016/j.ccr.2018.06.017

Cited by 62 publications

(52 citation statements)

References 83 publications

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“…Methyl orthobenzoate was purchased from Sigma Aldrich (Seoul, South Korea). Solution-state 1 H and 13 C NMR spectra were recorded at room temperature on a Bruker Avance III HD spectrometer operating at 400 MHz for 1 13 C). Splitting patterns are denoted as follows: br, broad; s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet.…”

Section: Experimental General Considerationsmentioning

confidence: 99%

“…Using general procedure B, monomers 1, 6 and 7 afforded 165 mg (37% yield), 133 mg (30% yield) and 129 mg (29% yield), respectively, of poly(phenyl carbyne) as a brown powder. 1 Monomer consumption analyses A total of eight 30 mL vials equipped with glass-coated stir bars were each charged with 4 mmol of monomer, 4 mmol of n-dodecane, 4 mL of anhydrous THF and in some cases 1 mmol of naphthalene. Seven of the vials were charged with 13 mg (2 mmol) of lithium.…”

Section: Poly(phenyl Carbyne)mentioning

confidence: 99%

“…A C1 polymerization is a reaction that grows polymer chains in single carbon increments. 1 Such a process deviates from the more common polymerization reactions that extend polymer backbones by two or more carbon atoms during each propagation step. Beyond the fundamental distinction, C1 polymerizations offer access to highly substituted polymers which often exhibit unique 2 or enhanced 3,4 physicochemical properties compared to less substituted analogues.…”

Section: Introductionmentioning

confidence: 99%

“…A C1 polymerization is a reaction that grows polymer chains in single carbon increments 1 . Such a process deviates from the more common polymerization reactions that extend polymer backbones by two or more carbon atoms during each propagation step.…”

Section: Introductionmentioning

confidence: 99%

“…Beyond the fundamental distinction, C1 polymerizations offer access to highly substituted polymers which often exhibit unique 2 or enhanced 3,4 physicochemical properties compared to less substituted analogues. Diazo compounds, 1,5–7 ylides, 5,6,8,9 isocyanides 1,10 and geminal dihalides 11 are typically used as monomers in C1 polymerizations because they are capable of generating carbenoid‐like intermediates that can condense in a repeating fashion (Scheme 1(a)). Catalysts are often required to activate the monomer and some offer controlled 12 or living characteristics 13–17 …”

Section: Introductionmentioning

confidence: 99%

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Poly(carbyne)s via reductive C1 polymerization

Cahoon

Goossens

Bielawski

2020

Polymer International

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C1 polymerizations enable the synthesis of densely functionalized, persubstituted polymers that are challenging to access using conventional methods. One class of C1 polymers are the poly(carbyne)s, which are unique in that they can adopt branched or linear structures, or combinations thereof. Herein, we report the synthesis of new poly(carbyne)s, including those that feature side chains with carbonyl-containing functional groups. The polymers were obtained by exposing solutions of monomers outfitted with trihalomethyl or trimethyl orthoformate groups to metallic lithium, and reaction performance was improved when electron transfer agents (e.g. naphthalene) were included. The mechanisms of the polymerizations were also deconvoluted and found to depend on the monomer employed.

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Section: Experimental General Considerationsmentioning

confidence: 99%

Section: Poly(phenyl Carbyne)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Poly(carbyne)s via reductive C1 polymerization

Cahoon

Goossens

Bielawski

2020

Polymer International

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Transition‐Metal‐Catalyzed Carbene Transformations for Polymer Syntheses

Ihara

Shimomoto

2021

Transition Metal‐Catalyzed Carbene Transformations

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Controlled Synthesis of Cyclic‐Helical Polymers with Circularly Polarized Luminescence

Gao

et al. 2022

Angewandte Chemie

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Cyclic polymers attract attention because of their endless structure and unique properties, which differ from the linear analogs. However, the synthesis of cyclic polymers is difficult and prohibits their functions and applications. In this study, we reported chiral cyclic Pd II -catalysts that initiate a living ring-expansion polymerization of isocyanides, yielding a single-handed cyclic-helical poly(phenyl isocyanide), with predictable molecular weight (M n ) and low dispersity (M w /M n ), in good yield. Using this method, cyclic bottlebrush polymers were prepared via the grafting-onto strategy. The cyclic topology was confirmed using various spectroscopic data and atomic force microscope observation. Moreover, the cyclic polymer brushes, comprising of a one-handed helical backbone, showed interesting photoluminescence and circularly-polarized luminescence.

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Metal-promoted C1 polymerizations

Cited by 62 publications

References 83 publications

Poly(carbyne)s via reductive C1 polymerization

Poly(carbyne)s via reductive C1 polymerization

Transition‐Metal‐Catalyzed Carbene Transformations for Polymer Syntheses

Controlled Synthesis of Cyclic‐Helical Polymers with Circularly Polarized Luminescence

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